top of page

The Number 1 Responsibility That Sales Leaders should Focus On (with Ryan Ketchum of Woven)

From being a corporate misfit to a business owner to being a sales professional and leader. Different roles with one main goal, to succeed. 


Ryan Ketchum is the Senior Director of Sales at Woven, a startup tech company designed to help other fast-growing companies seamlessly hire great engineers. Before working at Woven, Ryan was first known as a trainer and successful business owner in the fitness world, building his skills as a great salesperson and leader. 


At present, Ryan utilizes his sales knowledge and leadership experience to help Woven achieve success.


In this episode, Ryan Ketchum joins us to share his experience and expertise in sales, coaching, and leadership to grow a startup business. Ryan talks about his different career transitions, challenges, and business realization and shares his insights as to what it takes to be successful in any career role.

Episode Highlights:

01:26         Ryan’s academic and professional background

05:20        The first sales experience in fitness business

09:32        Selling the path to customers

13:17          Leveraging network and creating educational platforms

18:03         How Ryan involved himself to Woven

25:42        Moving backward with career title

34:27        The importance of coaching time for organization

38:11          Ryan’s characteristic and responsibilities in his different titles

44:45       The impact of mentors and coaches

48:34        Woven’s product market fit development

01:04:51    The passion to win but win together

01:08:09   How to be successful in your leadership career

Ryan Ketchum:  31:05  
How important is that coaching time, I think it's probably the most important thing that you can do. I think that I split up your kind of leadership and there's four boxes that are kind of a grid. On one corner, there's your mentor, let's call it trainer, that's more your management, do this, this is how we do it, do it this way, holding people accountable to whatever their KPIs are, whatever they you know, you're tracking for activity, those things. There's this trainer, I'll show you how to do it. 

Yeah, that management, like hold them accountable piece, you've got the coach, which is then help them discover how to do it, get them to realize, here's the potential. And then there's the mentor with like, let me help you out with your career help you see these next things that are coming, I'll share what kind of how you've got there before I spend a majority of my time in coach trainer mode. But this right now, and it ebbs and flows, I think in a leadership role in a really fast growing company, you go through periods of time where you've got to do aggressive hiring, and you're not getting as much time with your team.

And you've got to have the team that you have clicking on all cylinders, and you're more management with that and a little bit of coaching, you've got then the time where you've got the team where you're running, and you're doing less hiring, and now you're trying to elevate and escalate. And it shifts gears based on priorities or what you're seeing in the company, you know, when rates go down, what is the next move? How do you get to the next level, but if you're not coaching your team, and you're not spending a good portion of your time coaching, and I think that just varies, right now, it's probably 25% of my time, just given like where I'm at. 

And I've taken on a bit of a new challenge as well, where I just recently in the last three or four months took on our CES function as well. And so now it's kind of like all revenue comes in and reports to me. So I'm learning a lot of that. So I'm asking them to train me more about what's your day to day, you know, I kind of know what you do. But like, let's figure that out. And then stepping back outside of that and coaching them a lot on what I think we're missing, here's some opportunities that we could be on. 

And a little bit less with the A's right now. So what ebbs and flows, but if you're not coaching your folks, and that is the thing, like when you're hiring, that's something I look for as coachability 100% of the time, it's the it's really difficult to work with that person that just wants to resist everything you're telling them or doesn't want to apply anything new thinks they know everything with it. And it's not that I know everything. But I get to see this weather, I have that experience. And I get to see this outside perspective of you doing your job that you don't get to see you're right in, I can share some things. 

And if they're not willing to accept that they're going to limit their growth all the time, which then limits your growth. So that coaching is a huge chunk of time that I spend with the team. And I think it's really important to do that, as a leader, especially in sales. That is probably in any role, but that's the one I'm most familiar with.

Grayson Faircloth:  34:00  
And you mentioned something that I wanted to come back to about titles and how like, maybe you're not like you don't care as much about the title, but it does do a pretty good job of representing, like what experiences that you've had, especially for future roles and stuff like that. The interesting progression with you is that you went from, you know, founder title then to like the VP of sales down to the individual contributor, and then back up to again, this like sales leadership role. And so I'm interested in things like the characteristics, responsibilities, the things that you're doing now, again, back is this senior director of sales role that you weren't initially as just as a role at Woven.

Ryan Ketchum:  34:42  
Yeah, you know, and all the previous before Woven, I'd say it's like, a very different leveling and titling now. You know, it's founder of a really small company making a million dollars a year. You're wearing all the hats, doing a lot of things, doing a lot of contract work to help you out with that. That previous VP The title was a little bit more like what I would be doing now hiring the team building the team strategy working at the highest level within the company, there are differences now are, you know, when I came into Woven is that a like my number one responsibility was driving the business and I could do as much else and I was in the room, they were six eight person company at the time. 

Like, at that point, your strategy planning is just like you're doing it month to month, if not week to week, trying to figure it out. Everybody's in the room talking about it. So it'd be involved in that. But it was more like, how do I make sure I'm successful in this, I've got to figure out how to be successful here, less worried about all the other impacts and everything else that comes in, I'm not thinking about a team, I'm not thinking about that. How do I put up my number so that we can survive and get to that next round of funding. 

And one of the things that's similar is that, I always put that on me as like, hey, everybody's kind of the whole rest, this team is relying on me to do this for them to keep their job, if I don't do my job, they don't keep their job. That is the skill that transfers or the mindset that transfers when you go to leadership. It's like if you're not doing your job really well, you've got your team of AE, SDRs, whatever it might be, that are all dependent on you to be able to keep their jobs and in turn, they've got to do their so that you keep your so there's a little bit of a trade off, there was a lot more like tactical boots on the ground, doing a lot more of the like day to day work in that eight year old. 

And then like gradually started to bring on a team even before that title, that's where you start to get pulled in a lot of directions. And this is where the like player coaches, you will talk to an advisor, a board member, anyone that will say player coach is a good idea. I am blessed and cursed with the mindset that like telling me I can't do something, I'll figure out how to do it. I was told that the whole way through our board had mentioned that to last last had mentioned it to me, it's impossible, we can't do it like you'll fail, it will do this, it's definitely a risk, you have to look out because you are putting a lot of directions and you're fighting against your own incentives, your own drive to hit your number versus helping lift up your team. And how do you balance all that out. 

And I just kind of pile it all and all that success is mine. But the overall numbers but I got a hit. And so like I get paid off of XYZ, that's fine. But I'm going to just mark myself against this number to drive success. So I started to learn a little bit more about that management. Now you have to have one to one and you have to do some training, you got to do call reviews with these SDRs, you have to do the hiring with that. There's a lot that goes in. So the data is very tactical, lots of me doing the work to now it is more, I've got to zoom way out a lot of times a week. And I have to look at what's the overall performance like what are our conversion stages for pipelines? What's the top of the funnel look like? You know, what are their conversion stages for their activity pieces? CSM is like health indicators. 
Now what's going to tell us about accounts at risk? How do we make sure we're on renewals, and you're trying to create processes that will cover all of these different people that might operate in a slightly different way. Because not everybody is going to do it all the same. And then you look at the team. And now you've got to go, Okay, here's the team. But now what are my weak points? 

And is everybody a weak point, or is one person a weak point with this, and you got to drill down into those individual people and say, where do they need my help? So it's just like multiple layers of zoom. And then the biggest challenge you have as a leader is knowing, even as a little bit of a player, coach, you're pulling a lot of directions, you can get very busy, as a leader, with an executive title, whether it's director head, doesn't matter, all your priorities change. 

Now it's company first. Now it is how do we get the strategic initiatives across while you still then hopefully, those tie into your numbers. And the best way it's explained to me is, you're going to have a million plates spinning at all times. It's not how you keep them spinning, it's identifying which ones can drop them. And it's okay, if they drop them break. And that's a really hard thing to transition to. And you come from that individual contributor role, where like, you can keep it all moving, and you got to have things clicking on all cylinders to now, what are the things I can allow to fail a little bit. 

So just like let that fire burn, it's not gonna be mission critical for us. And I have to work on these things. And just ignore that for a little bit. While we do this, because this is the thing we're betting on right now to help succeed. And that's probably the biggest challenge because now you're just thinking about the big picture. And you always have to keep that in mind.

Grayson Faircloth:  39:34  
You mentioned a lot of things we could dive into. But how did you learn about these things? Like how did you learn that? In the fitness industry? Maybe you don't care about conversion from stage one to stage two of the deal pipeline? Where did you learn about these? Or like, how did you pick these up over time? Were there more mentors like you kind of have in the fitness space? Or is it a lot of like reading books or how did you get there?

Ryan Ketchum:  39:54  
Yeah, over time. I've always been a learner, always been seeking information. So it's a mixture of all of those things. Water books, I remember reading the sales acceleration formula back in my fitness days and trying to figure that out and how to build like kind of a pipeline and a marketing funnel and all the things that go into that. So getting a lot of exposure to that early was great. That information is awesome. But the things that have made the biggest impact for me are mentors and coaches. 

A pivotal moment in the career journey was when I started working with Robline, Lucien & Associates, so to Indianapolis company, they help with the key of audio sales, that is sales, training, coaching mentor shit, but it's also very much geared towards like entrepreneurial, there's a bigger scope to it, and they tie in the whole person with it. Getting that exposure to someone that sees all of these different businesses and gets to see how everything's set up and has a different way of thinking about things. 

That is where I learned the most. And credit Rob's kind of the breakthrough in my sales career. It's where when I was doing consulting in the fitness world, we were able to take it from, like really just like barely keeping our head above water. We were in like, deep, we weren't gonna go out of business. But we were struggling to hit the growth goals that we needed to have, it was really challenging to really accelerate that to where we were doing 2 million a year in sales driving that up. And it was all because of the things and the processes and the strategies, tactics, all that that I've learned. And the thing that I did is I dove headfirst into that I had him as a coach, they do training. 
I was at every training that they did, I went to every Leadership Forum that they had to connect with other leaders and get their ideas with that. So I was always picking people's brains on what they do? How does it work in what's different? How can I apply that to what we do? And along the way, I've had different coaches, I've had executive coaches, leadership coaches, fortunate now to like I still work with Rob to this day, that was a thing where I brought him on, as soon as I was able to hear it Woven, it's where we saw a giant spike in our top of funnel and hit our growth goals. 

And then had a chance to work with Ryan Williams. Now as an executive coach, that gives me that outside perspective, like, here's what it's like to be a tech executive, here's what you have to think about your next step in your career. Don't go into the people, it's like we all have to walk a path. And we're all going to make a bunch of mistakes, how quickly you learn from them is great. But if there are some big mistakes that I don't have to make, and like those landmines that might just enjoy your career. If I can have somebody go, Hey, watch out right there. Don't do that. Watch out over there. 

Don't do that. Or, hey, there's a different way around that. What have you thought about this, having that been able to learn and apply it has been the thing that just changes my career. So you get to avoid so many of those hiccups and learn along the way without having to do it the hard way. So the books are great, I think you should read them. I think there's a downside to reading too many books, you can just consume a bunch of information, whether it's podcasts, books, whatever, there's only so much you can apply. 

And it's great to have that information, I find myself going back to the books that I read five years ago, reading them now. And it's like, totally different book because of the experience. But it's really been those mentors in that because it can also hold you accountable, you feel a little bit more connection to him. And that's been the game changer for me.

Grayson Faircloth:  43:17  
Ya know, I've heard so much about like, that is kind of how you shortcut. These people have the experience that you want, and they'll have to help you. But you have to find them. And that's probably like the hardest part is finding the good fit. So Robline and Ryan Williams for people?

Ryan Ketchum:  43:33  

Correct? Yeah. Cool.

Grayson Faircloth:  43:35  
The next thing I wanted to dive into a little bit was this idea of ideal customer product market fit. It's something that every early stage company kind of deals with. You already mentioned that you joined Woven kind of pre product market fit. But so what was the ideal customer back then? I know you said startups, but talk about like the actual ICP, it was a head of engineering at a certain startup and kind of how did that definition develop over time?

Ryan Ketchum:  44:01  
Yeah, so what we looked at is we're very, like count focused, what we realized really quickly is, you know, our product is good for certain types of companies that value it at certain stages. So early on, when I started, we looked at companies that had raised some funding, and it should have been 1,000,002 million. So we need to see them raise some funding, we saw that was a great indicator that they're going to start hiring but this and then we drill down into our target within that was the head of engineering, like what's the senior most engineering person there? And we've actually had some disqualifiers, early on, where if they had a technical recruiter that we would not prospect into them with this and a lot of it was because we had trouble tying the value to that we were seeing as a little bit of competition that didn't need us as much and we're still figuring out messaging at that point. 

So it was a lot of seed theories, a type of company that we did sort of work with and the plan was to get into those. And as they grow, if we do a good job, we'll stay involved with that. And then it's a lot of exploring and trial and error with it, then you figure out the market isn't, you know, eventually run out of time with that market, you've got to learn how to sell into these other areas. So then we gradually opened up, okay, now we're gonna say, Oh, we figured out how to get in. And we got a couple of deals with people that had technical recruiters and a recruiting team. Great. We know how to do that. 

Let's open that up. And we just gradually started to go up market a little bit at a time and kind of shift messaging with what we're doing and where we're having success and tracking, like, what's working, what's not working? Why did we lose this deal? How did we get into this deal? What did they say three months after they started about the value? And now we're at a point where strategically I mentioned, we moved up market where we've labeled established tech is the key area that we focus on, we start plenty of startup SMB companies within that, but the established check market is kind of just shy of enterprise. 

And the keys with that is like they have a large software engineering team of 100 or more. And like a dedicated VP of software engineering, the thing we know is, it's really hard for us to tie value into someone even if they have an engineering team, or they're a little bit of a tech company, where that is not the core of their product. And that's not the big focus, they have to value bringing in really great engineers with this. Whereas like, you know, banks, they'll hire engineers, but maybe not at the same level that the aggressive startup is going to be or these established tech companies that we would focus on. Now we still focus on engineering executives, so directors and above are our primary targets, we know we have to get to them to win a deal. 

We now also can loop it and go on the talent side of the house or HR side of the house and look for those executives as well. So it's expanded, and then that adds complexity. Because now we have different segments, we have different personas within those segments, all those personas present with different problems. So now you've got to train your team on how you quickly identify segments, problem persona, the talk track for that, or what's your pitching your value prop for that, because if you miss a line that you're gonna lose more deals than you end up winning. And so this continues to add complexity to it. But that's part of the fun.

Grayson Faircloth:  47:21  
A lot of startups, you know, they start in that place of pre product market fit. And you obviously joined in like we talked about before you got to that point. So what kind of things would you recommend for like early stage A's or sales leaders that join on these like pre product Market Fit startups to actually like, find their place? Like, what did you guys do? I know, you mentioned like, reviewing deals like reviewing Why did we lose this deal? Like, what are they saying a couple months after that, and those I think are great. Were there any other things that you kind of thought were pivotal in determining, like in kind of improving on that ICP and kind of getting closer to that what you consider like product market fit and eventually hitting it?

Ryan Ketchum:  48:03  
Yeah, number one is listen to your customers and prospects, you get the founders curse with a lot of founders that come in, where they've got their idea of where this fits. And they may have an amazing product and amazing idea overall. But what they think the value is may not be what the prospect or the market thinks that value is or how you need to sell it to them. So it's listening to them. But I think the fastest way we learned was we weren't afraid to try new stuff. And we had a lot of people involved in the process. 

You've got to bring a lot of people into it, where the engineering and product and engineering team has to be ready to hear the feedback for this is what we're missing. This is why we're losing deals. Here's what people are asking us in calls, doing the debriefs on deals that you lose, we would refactor every call that we had just the fear of what did they say? How did they say it? What were they telling us they were trying to overcome? Even if we didn't have that fit? Yeah. And with this, and then it's about sharing it with everyone in the organization. So we can continue to build that product towards what they need. And then you have to prioritize what's most important, your work? 

At this point, still, we're making, we have some work to do to get really great product market fit overall for that, like enterprise level, that's a way different product than what the startups need with their so we have to do that same process, almost every market you go into or every segment you go into, you've got to figure that out again, and how do you tie it in and then prioritize? What are the things about that product market fit you need to create the generate that move the needle in there, you need to you know, for us we look at okay, top of funnel is still the thing we want to drive most, what are the things we can create the features we have built the product that says we can get more top of funnel because of this not necessarily with expansion or stickiness? 

We do a good job there right now. So that's making those trade offs so it kind of goes to align what are your biggest challenges or initiatives as a company? Okay, where's the product now and be really honest with us? Golf With where it is. The other part would be very transparent with your customers early on. I probably can't count on both hands, how many customers early I told, I don't think we're a good fit right now for you. I don't think we knocked it out of the park that have come back. And now that we're ready, their customer had been there for a long time with us. So being transparent also helps you see like, they'll help you tell you what you're missing. If you oversell it, they might churn and you don't ever figure out why. But you'll tell them upfront, though, you'll say, here's what we do really well. 

That's it, we need these three things today. We're not there yet. Is that okay? If it's not, no big deal, but now you know the things and you started to compile that information. One thing I wish I would have done better early on was track more of this and CRM or keep tabs and make it less ambiguous. It's really hard to do early on, but you create those buckets, or whatever you lose, lose the deal. And you create these different areas, you can kind of start to categorize your data, because it's there. But a lot of times early in the process, it's hard to figure out how to put it all together and make good decisions later on.

Grayson Faircloth:  51:08  
Yeah, totally on board with you. They're given automations background, everything I want to, I want to keep moving, there's a couple more things that I want to hit on that I think would be really interesting to hear your perspective. So how has the sales team evolved since you started? So you mentioned that you guys brought on SDRs, pretty early on, you k
ind of took on more leadership roles, and then brought on more now it seems like kind of the customer team is reporting up to you as well, like, so how has that kind of evolved? Since you've started? And kind of like, why did you choose to add, like SDRs versus having ease to the prospect? And like, just what were you thinking, kind of as you kind of just grew the organization as a whole?

Ryan Ketchum:  51:50  
Yeah, there's lots of trade offs to be made here, you decide that so as we went on, early on, I was full cycle a and so prospecting, figuring out how to build the pipeline, what could we do, and then also working those deals at the key point where like, was driving some pipeline, but then in the deals, you're pulled in both directions, and we did kind of a quick evaluation of, like, where's the most energy applied? What's the highest skill type of effort we need to have? Also looking at cash burn business impact, what do we have there? 

It was like, Okay, I was figuring out how to sell it, like we're getting ready to close deals, but I had to spend a ton of time building the pipeline, we're still figuring out messaging, still, we can bring another ad on, and then they're gonna have to learn how to sell and how to prospect this. And that's an option. And you can run all full cycles with this, because our deal size wasn't large at the time, you know, 10k to 15k, on an ACD. for that. So it's not like not an unreasonable thing to think an ad should build their own pipeline. But we did see the amount of energy and effort that it took in the volume to get the prospects and, and so we doubled down and said, Let's go hire three SDRs kind of know in the normal model that and again, this was a thing I fought back against, like, you'll hire three, one, I'll stick. 

So I brought three on and said, We'll train them up and we can get more pipeline, I can then handle the pipeline and just coach them when the pipeline gets full, then we'll talk about AES. And I think we have kind of a lopsided model on the SDR to SDR to AE side. But our retention rate and net revenue retention is so good that we get the payback period on those SDRs is a good ratio for a fast growing startup. So we made that bet, that's what we're going to do, because we thought that will drive the top of the funnel to get the revenue, which was the most important where if we brought another a, you know, two on, maybe they wouldn't stick either. Now we're just on the same path, but I'm doing less because they don't have as many opportunities. 

So we brought that on. And then the bet was, I'm going to drive it as fast as I possibly can. And I'll take as many deals, I think I got to the point where I was running eight to 12 conversations and demos a day. And just at that point, you can't keep up. I used to live with that and it was a lot better. Now it's time to go hire the AEs to build that out. And I did promote one of those bursts SDRs at that point. I said, well, I can't do all the things with the SDRs so the promoted ones have a team lead where he was one of the first hires now he was gonna run team lead for some of the new ones we had. I went to work to hire the AEs and we hired two of our first A's and said, okay, we don't know, are they going to fit? We'll bring on two A's to get that and then now you're watching pipeline data. 
So it's like is your top of the funnel enough to feed your AEs? What's that balance always thinking trade offs? And what do we have to do? What's that next hire to make by bringing on a new ad that just dilutes the pipeline now you've got three P like pissed off AEs because their pipelines are not there. See your balance and all that as you go through? And then you start to look at it like, where's your time? Gotta go and then there Also things like what are the only things I can do? So right now I know I have an SDR manager that has seven SDRs. He can do that if he's done that same team lead. So it's been with me for a while. We've tried a bunch of different functions with this. 
At one point, I tripled the team, we broke every process and system, everything fell apart. Like we just everything broke, had to go back. And so it was scaled back down. Let's reconfigure. And let's see what we can get out of that. We've had different structures on that team that we've tried some of it's trial and error, sometimes you find out that people aren't working, then you figure out like what can only you do as that leader, and I'm the only one that can train and coach those A's right now, there's no one else on the team that can do that. I'm the one that knows the pipeline, how to do it, how to move the win rates. 

So I work directly with A's they're my they were my priority: help SDR managers with the SDRs keep them moving. And then we did have to go through a bit of a restructure. We had to look at this, like forecasts, we looked at our cash run, right? And said, Okay, here's the different plans that we're going to make. Here's the changes that this you know, the environments gonna have I told you, we made the shift to that mid market, and we're having success with it. What we said, Here's what the team looks like now, because after a fundraise, you build the team really quickly after what you plan it to be in 12 months. 

We raised the money last November, and by February, March started to see these trends. And now you go Wait, I don't know, if we meet that team. We're not going to hit that number. Yeah, we got to look at what we need for this. And so it's less about the people, it's a sucky thing to have to do. And you have to look overall at the business, you hopefully do it in a way that's empathetic and humane for the people that you do have to like, know that you had to make this decision. So we didn't have to make a tougher one later on. It said we made the right bet. So then it's like, well, what else can I do is like I can help with the CS team. I know enough about it, I can do the renewals. 

So now my focus shifts to new business renewals and expansions. Those are those two revenue drivers, I've got to be able to oversee that. And then you have to gradually make those trade-offs of what can someone else do? Can you level someone else up on the team? Is there an opportunity, you're looking for that next leader that might want to step up and take on a little more than what they're doing now while still maintaining this? So there's a lot of those trade offs. And now the structure looks like I've got my small team that I work with these days and then the SDRs. 

From that, which is a lot to take on at any point in time, I've had 2023 people reporting to me, yeah, it gets to be a lot. Now I've got, you know, right around 14, that report. And so you can kind of ebb and flow as you go through and you start to evaluate, like, again, you go back to that, like, at this level, it's like you care about the people, it weighs on my mind all the time. That is everyone's job at Logan is my responsibility to drive this revenue. But there's also company firstly, that the company doesn't exist again, nobody else has it. So you've got to think about those things. And then zoom into like, how do I make that happen with the team that I have?

Grayson Faircloth:  58:05  
Yeah. So and there's so this is an interesting question given now that you kind of oversee the customer side of it. But how do you as the revenue leader work with the other departments? So I'm guessing there's also some sort of marketing function within Woven as well? How are you making sure that it's kind of like one revenue goal, and not like a marketing goal and a sales goal? How do you guys approach that?

Ryan Ketchum:  58:28  
Yeah, so like one of my personal values, and the thing I've set on, my team is passionate to win, but win together. And I want every one of my reps to want to be the top, I want you to want to strive to be that top performer, and want you to want to win, but we're going to not hold things back, we're all aiming to the same thing. We're going to elevate each other up. And I carry that through with my peers on the leadership side. So we've got a marketing function, we've got product and engineering across the board to have that. 

So we're really collaborative in love and we've been that way from day one. So how I work with those folks, we do consistent check-ins with that. We all do one to one whether it's weekly or bi weekly with my peers across their departments and functions. We will do alignment meetings with this where we get marketing and sales alignment, make sure we're all working, here's what we're here. And here's what we're seeing, here's what we're doing. And a lot of it comes from the top down leadership, Wes is really good about tying all of it together, getting us to be collaborative. 

If someone has a problem in an area, we all jump in to help fix it and give on and share what we can with this. So it all starts at that leadership level. But you have to be willing to do things that you can't be and I've always been the sales leader that says like, marketing sales have the same goal. I don't want us to bicker, there's always going to be a healthy amount of friction, marketing, sales, sales to CS, product engineering is going to be not happy with all the things we request. They'll always be that. But when we're all aligned on the overall goals for the company at the leadership level. 

We all know what it's going to take to get there and we all want to drive towards that. It's really easy to be You collaborative with that and jump in until it's the point, it's like, you have to be working towards that, like, there's no reason to bicker about it, we can give feedback, we're really direct, we tell things that we don't like, we're going to share that. And one of the ties back to some values, one of our values is a woman's candor with care, something that I really brought in. 

I think I hopefully drove a lot this way. I'm going to be really direct with you, but I'm going to give you the feedback you need. Because we're all working in the same direction. I care about you as a person, I'm gonna deliver it hopefully, I don't always do a great job of this, but deliver it with like, the empathy and care so that you're receiving it well, so that it's a growth and we're not always going to agree on it, like we are going to disagree and get some arguments, we have to put that aside and say like, okay, cool, we all we agree the goal we're gonna go after, and we all do it. This is some of the culture and just how the teams work. 

And then it's about the leadership showing that like, we're all going to be in this to move to the same goal. And that means we have to work together and have to work cross functionally. So there's a lot of that a little bit and everybody jumps in, I feel very lucky to come into a company where everybody knew sales was driving the number early, like sales was the thing we had to double down on or nothing existed. And now we just have a much bigger team. And people still know that revenue matters. And that comes from all different areas.

Grayson Faircloth:  1:01:17  
Yeah, no, I think that's like a realization that a lot of successful companies have had. So it's good that you guys are kind of on board chugging along there. And I want to end it with one last question. So the purpose of this podcast, like you and I mentioned at the beginning, is to help those people who are in individual contributor roles, or maybe just early stage leaders. So I'd love to hear about people who are maybe either at Woven, or just in general, if you're having a conversation with them, like what are you talking about in terms of progressing their career? Like, what kind of things are you having when you're having those conversations with your team? Or just in a hypothetical situation? If it's not something that's currently happening?

Ryan Ketchum:  1:01:56  
Yeah, so I'm a big advocate for this. As a leader, I have career conversations with my team. At least once a month, I was four minutes late to jump on board, because I was on one of them. Robert, I just want to know what motivates you? Where do you want to go? I don't try to steer anyone in this? I want to hear like, where do you think you want to go? And then you've got to take kind of like, put your sales hat on and go two or three layers deeper? Why? What about that? Because I think you get a lot of canned answers, especially from people just starting out in their careers, just getting into this. You know, it's like, oh, he ordered management, like, you're gonna hear those two things. 

I want to manage a team on this. Why? What about it? Okay, well, here are the things that have to happen for this to go on. Here's some of the skills like Are you ready for that? Here's some gaps that we have. So a lot of it is about, like, what motivates them? Where do they want to see themselves, you have to truly understand why. And then this kind of tie into the coaching is kind of helping them see the work that they're going to have to do to make that happen. And then you've got to have those conversations. 

And then as the leader, you've got to remember what your job is to support them to provide them with the opportunities to go get that whether that's outside coaching to help them level up before they're ready resources now projects that they can take it on, loop them into things that they maybe they don't have to be looped in on on decisions or projects where they can see how some of that interacts and get them that exposure with it. But it really comes down to like, you can't guide anyone to a direction they don't want to go, you have to find out where they want to go. 

So it's open ended conversations. And if it's, I just want to be in this role. And I'm really happy. That's okay, too. That's not for me to decide that that's for them. And then when I have those conversations, because I have them all the time with my coaches, things that have helped me also are like, what's the end game? Like? Where do you want to go? What do you think that really is? And you got to stretch people out to like, maybe beyond what they can think about so that you can at least start that idea. 

Now, in an early SDR career, what do you want to be in five years? It's impossible to think about or how much do you want to make? So you've got to guide them in that and you know, there's a billion tools and frameworks to get there. You know, I think it's big and then having people write that down. You write it down so that you can keep tabs on it and come back to it. When you get there. You got to be having those conversations, and it's mostly about what they want and why.

Grayson Faircloth:  1:04:27  
Well, yeah, thank you so much. Yeah, I think you're a really lucky team underneath you. They're Woven. So thank you, Ryan, again for hopping on the podcast.

Ryan Ketchum:  1:04:35  
Now, thank you guys. Sounds great. I hope people got some value out of it and were able to share some insights and are always happy to help anyone out if they have questions.

Grayson Faircloth:  0:01  

Today we're joined by Ryan Ketchum. And this episode is particularly interesting. Ryan is someone who clearly had that entrepreneurial drive from early on, but didn't actually move into what we would consider the traditional tech startup world until almost 10 years after graduating. He currently serves as the Senior Director of Sales at Woven, a company designed to help other fast growing companies hire software engineers. 

And in this episode, we cover a couple of different things we cover, you know, his transition from student athlete way back in the day, to gym owner, and to now, his current role as a startup executive. We talk about learnings on the way, one of those learnings being the number one responsibility that sales leaders should be spending their time on. So if you're interested in hearing about that, and Ryan's background, and everything else we talked about, stay tuned. This is a good one. Let's get started. So I'm here with Ryan,

Ryan Ketchum:  0:54  

welcome. Hey, Grayson, appreciate you having me on today. I'm excited.

Grayson Faircloth:  0:57  

Yeah, I'm excited to dive into some of this. We've got a particularly interesting background, coming from fitness and moving into sales and working for a startup. So I'm excited to get into that background. But I'd love to just start off with some general background on yourself. What brought you to and like what kept you here? How did you get to this point, just real quick, and then we'll dive into the details throughout the rest of the conversation.

Ryan Ketchum:  1:21  

Yeah, the high level like flyover, I came to Indiana from Kansas for college, and went to Indiana University as a track athlete there. And so I ended up staying in Bloomington after that, and started my fitness businesses, the things we'll talk about and a little bit more of that background, a couple of businesses there and then moved up into the Indianapolis area.

 After I had started our family. And we moved up here to be a little closer to my ex wife's family. At the time, a little bit more help turned out to be fortuitous, because we ended up needing to help them out a little bit through some health challenges that they had, and then have been here ever since. So it was a lot of just like, natural path. 

I knew I wanted to get out of Kansas, landed in Bloomington and then moved up here to Indy. And the rest is I guess we'll dive into the details as we get into it, but no, like, particular reason personally other than family stuff to be up here.

Grayson Faircloth:  2:22  

Cool. And you and I actually share a love we were both at IU. So I'd love to hear, I guess it was your very first experience with sales. Was that down in Bloomington at IU or were you like pre college involved in the sales

Ryan Ketchum:  2:38  

world, I have kind of the typical story of like an entrepreneur started out. So I can remember starting a lawn mowing business when I was like 10 or 11. Like putting stuff in the church bulletin to get clients knocking on doors, trying to get leads going to that and making my parents drive me around with a lawn mower in the back of the car to mow the lawns because I couldn't do it myself. So we've kind of always had that and didn't really know what it was. Yeah, so there's a little bit of sales with that. I've never really thought of sales as a career. Why honestly until later in life, but started after school. 

After I started my last semester of college, I knew I didn't want to go to grad school, I had a rare idea of what I wanted to do getting recruited to go to college. And I was really fortunate to be the kid who didn't have to try that hard in school and got really good grades. So everybody pushes you to like business or med school or something like that I didn't really want to do either. Those who started out in business at IU and hated it, like absolutely couldn't stand it didn't want to go to class. 

And so flipped over and started in their kinesiology program after that, and kind of had plans to be a strength coach after college and see where that would take me being as close to I was as an athlete to the strength coaches, I saw all the politics that go on with that how grueling that Job was for any sort of opportunity. I was like, I don't want to do that. So I didn't really have much of a path after college, and was lucky enough to kind of be good enough athletically to potentially pursue some things after college, far from professional athlete with that, but pursuing like National Championships, Olympic trials and things like that, and in my last semester, because I didn't want to go to grad school, I'd had like four credit hours, and that's all I had to take. 

And so during that time, I also started training young high school athletes. And so that was probably the first like sales experience that I've had was you got to sell people on why you Why would they trust this college athlete to train their athlete and started my business there's when I graduate way that I just continued that on, I had a good friend that had started a career with that. And so I started my own business renting space out of a gym. And that's when it clicked was okay, you gotta be able to sell these clients to get you to pay. And I can remember my first cell to this day, they just rolled over on me, it was super easy. 

I was as nervous as you could be, I couldn't believe somebody was cutting me a check for the amount that they were to like, train their kid to play a sport, and quickly learned that you had to get good at that part of the business. If you wanted to succeed, the clients weren't just coming to you, I didn't have the gym feeding the clients, I had to find my own. So I was really successful in that. And so to just think outside the box, you quickly realize you're trading time for dollars, every hour session with one client, you have so many hours in a day before you just burn out. If you're not working, you don't make money. And so started really early on, this was 2006 2007 when I started doing semi private training. 

So I'd say I'll just trudge to Santa now. And I'll train two or three people on individual programs at the same time. That didn't have to be friends, we didn't split the cost of the session, like they're getting the same value. And so this was before a lot of that had really taken off. So to figure out how do I sell that to them? How do I convince them that this is a good deal, this is better for them. And I got to be aware I was successful enough in that, that I was running out of space, I was really irritating everyone else in the gym, because I was taking up a bunch of space with my clients. And so I said, Well, the next step is start your own fitness business, and start that quickly then realize fitness professionals and people out there, there's a dime a dozen, there's 100 different methodologies out there to kind of rotate through. 

I didn't feel like there was anything special to offer on that side of things. But what I was good at was learning how to run the business side. The big part of that was how do you sell? How do you retain clients? So when I started that gym, that was my role, I tried to work myself out of being a trainer into that, then hiring other trainers to come on teaching them how to sell teaching, eventually general managers people on the sales team, how to sell that, how to run that business. 

And then that led to me doing more consulting and things like that. So I've just kind of gradually progressed through my years and kind of figured out like this is a thing that I was good at I really liked and that I think I had some value to deliver to some other people. So it's been kind of a weird transition kind of fell into a sales experience. And I think we'll get more into the like, how did I actually get into sales in a startup environment, and how that all transpired. But that's kind of where the lightbulb really clicked off. I feel like I figured out what I'm really good at. But I think I'm really good at it.

Grayson Faircloth:  7:56  

Was there a moment when you realized that? Well, one way? How are you pitching this to these high schoolers? Were you saying, oh, I'm a college athlete, I'll train you, you'd be like me? Or is it more like you want to like, this is you now? This is what you could be like, when did you realize that maybe there's different ways to sell and speak to different audiences and stuff like that?

Ryan Ketchum:  8:16  

Yeah. So you know, with parents of high school kids, everyone's aspiration. We all hear about, you know, the crazy sports parents that want their kid, everybody thinks they're gonna go pro. I think you're, you're silly not to use whatever you have in your experience to sell into the market yourself. So I definitely leverage that because you don't have any results. You have no clients. I know what I'm doing. I've been there. I've done that. And you use that. But you definitely then I quickly realized that you have to sell the path. 

Here's where the athlete is today. Who's the areas that I think that they can improve upon, based on my experience, my knowledge, my education, here's the plan to get them there. They get them there. Here's what you should see from that. So it's no different than any sales experience, whether you're selling b2b software is done b2c, anything, you're painting that picture, you're creating that gap for them. And you're showing them like, here's what you could be if we work with me. 

And if you don't like maybe you get here and maybe you know, I don't know, here's what I have to offer. So that was a really quick realization. For me, I think to figure out like, how do you tie that value? How do you figure out what their challenges really are? And how do you help them solve that? Or are you the person to help some because there were certain things that I think I realized quickly, you don't have to be everything to everyone, either?

Grayson Faircloth:  9:35  

Sure. So I'm interested. You've got a couple of fitness industry experiences. So it was that first one was that force fitness? Correct?

Ryan Ketchum:  9:44  

Yes. So that was my studio that we had had that was like post the gym when I was just kind of like my own little entity with myself, but force fitness was the studio and we had 6000 square feet eventually like garage gym space, started that into 2008 Maybe like the worst time to possibly start a business or things that require disposable income, but like too young and dumb to realize that and just saw an opportunity, and you make the most of it.

Grayson Faircloth:  10:11  

Yeah. And then the next fitness frontier, you've got a whole fitness journey that precedes your startup life. So you went into vertex. And then what was different about vertex like, what was kind of the progression there?

Ryan Ketchum:  10:24  

Yeah, so there's a little bit of overlap as we go through. So I was still running the gym, got to a point where I had the gym running kind of on autopilot. And while I was running the gym, I think I realized it really early on. I mean, I think this is any successful professional, I don't know everything. And I can either learn the hard way and figure it all out and hope I figure it out myself, or I can go hire people that have been there, done that and consult with me. So early on, I hired some business coaches, specific to the fitness world. I had a lot of mentors as well, that's one great thing about personal training is you get to work with some very successful people who build that relationship. 

And they're more than happy to let you pick their brain and get to know how they were successful as well. So those business coaches, I started with them, and had a lot of success in their program and became really good friends with them. And then started taking on some projects and helping them out as well, which was fitness revolution, and fitness Consulting Group was kind of the same company within that. So while I still had the gym, I started doing that, and then helping out like running coaching programs, helping other business owners sharing things like our systems, our processes, what we were doing, to help them grow. So I was doing that at the same time. 

And then when I sold the gym, then the very next step was it was at vertex and what that was more of an online program. So I went more and shared more of the training principles, a lot of the business principles that I ran, ended up doing and transitioning from a lot of high school athletes to like transformation type programs. And so I shared a lot of that information. And a big part of vertex was also leveraging my network that I built up in the fitness world to do interviews and help sell other programs that these other people had had out there with the audience that I had eventually built up with that. 

So that was more like an educational platform that I started alongside the partners that I had while still doing the consulting. And so it's like, I don't know, I tell people, I'm a glutton for punishment, I think a lot, like always taking on a little bit more than probably what I could handle a little bit of chaos. I thrive in that kind of environment. And those experiences help set me up for life in a startup world as well.

Grayson Faircloth:  12:41  

Yeah, that was like you went from founder and kind of owner to like VP of Sales and Marketing. Correct? And what, like, what sales and marketing were you doing at this kind of like company,

Ryan Ketchum:  12:54  

I guess? Yeah, so fitness consulting, or which eventually, like transition to fitness revolution with that, at one point, I was a partner in that. And then my responsibilities were the VP of Sales and Marketing this. And at one point, we had, I think, 14 different brands that we managed. So we had the Jim consulting, that was our primary driver. And then we had equity stake in all these other brands. And it went from everything from gym franchises and licenses where you could license the name and the systems for this all the way to like equipment and educational programs. And model was, there's usually a figurehead for each of these that is really good at delivering the message. 

They're kind of the face of it, the best way to tie it together would be it'd be kind of like an Instagram influencer or someone that's really good. Like they're sharing their information, they've got content to share, but don't know how to run or they don't have the interest in operating the business behind the scenes. And so we would take some equity in that. And then I would run all the sales and marketing for all of those. So I got experience doing everything from E commerce, to phone sales to everything in between how do you sell equipment versus information product? How do you write long form copy, email marketing, social media marketing, I oversaw all that for all up to the 14 brands. 

And then gradually, we transition to say, we're spread way too thin. And so we kind of sold off our equity, got rid of those other 14 brands, let them go on their own, got them set up. And we're solely on to the business coaching and consulting part for other fitness business owners. And that's really where I got the chance to build out a legit team for that, that one thing. So I would be everything from kind of the face of the company. 

Then with that where I was out doing the social media, I was out speaking at conferences, delivering the trainings and then we hired a team of coaches that would be similar to like a CSM in the startup world or an account manager where they worked directly with the clients we sold and a sales team that would go sell the customers with this, while also running kind of our lead generation would be like we'd sell products. So we'd strip out parts of the system and sell educational information. 

And we had a membership site that we sold into that then was kind of the base for this on our prospects for the coaching, once we got them into so a lot of complex moving downwards, team how to scale it up fast, I learned a lot about the downside to like the fitness world is that there's not a whole lot of money to be made in there. It's like it was always a passion. I love it. But you had to learn how to like to find and train up people that were not paying the salaries at a startup, or a CSM would get paid, you have to figure out how to train them up, get them excited about it, and for them to do a really good job. And I think that skill set and learning that I've made a ton of mistakes along the way has benefited in my journey as I went into the startup world. Yeah,

Grayson Faircloth:  16:01  

I'm interested because you go from selling to, you know, maybe in consumers, you're selling fitness products, probably a lot of different people then kind of what you're selling to Woven, so more of those engineering leaders, probably very different personalities. But so let's give a little background on Woven how you got involved with them. What was the company like when you got started? Because that, like you were saying, is your intro into the startup world?

Ryan Ketchum:  16:27  

Yeah, so kind of the intro and how I found Woven, as we started that as I got really burned out on the consulting piece, I was on the road speaking 2025 weeks out of the year traveling not the full week. But the 20 of those weeks, I was on the road flying around doing something driving, running groups, and really struggling to like keep that all moving balance that with family, I just had my son he was like a year or two old wasn't home a lot for that we had an office where we were there. 

So my life looked like it was up at 4am to the gym, workout shower at the gym, go right into the office, because I had from about 6:30 till 8 to do any creative work that I was doing. I was still writing a lot of the blog posts doing a lot of the marketing writing copy, then I go right from eight to five or six, whenever the day ended through the day with meetings and helping the team out doing whatever I could their commute home, get home, turn around, start doing all over again, and then be on the road in between that. And it's got to be really burnout. So how to talk with a partner at the time and say like, hey, like, we got to figure out how this changes. It's got to be more lucrative, like something has to change. 

We just couldn't figure out exactly how that would work. So, so cool. I'll just like you combined me out. Let's talk about it. I'll do a transition, we'll make that work. And I remember when we talked he said, Well, what are you going to do next? He said, I have no idea. Like, absolutely zero clue, I'll figure it out. And when I sold my gym, I was like, I don't know how this is all gonna work out either. It's like, I'm not a very risk averse person. I'll just jump in. I'll figure it out on the build the plane as we land, the whole thing. 

So I went to my advisors and mentors, and I was really lucky to have coaches, mentors, a lot of people around me that I trusted, and I had conversations with them. Here's what's going on. Do you think you know me well enough? What do you think I should try? Where do you think I'd be a good fit, like, just give me some guidance. And like 10 out of 10 said, absolutely sales, I would try like tech sales try to get into that environment. All right. So I started looking around for those jobs, and had a pretty quick realization like you're not going to land a VP job at something like this, you're not going to land a management or executive level job with no experience with that. And it's a different four. And I was totally cool to take a step back and say like, let's just start out as an individual contributor, interview the few companies that just weren't a fit. 

I tell people to this day, like I would be a corporate misfit, put me in like a really large company, putting some of this really well established, like somebody telling me what to do just follow this process, I'd be gone in three weeks. So I was looking for something different. And I didn't come through on job boards, like five or six times like not on this. Understand I don't get it after, you know, six or seven times. I don't know, maybe the universe is trying to tell me something. So I submitted an application, went through and then had the first conversation with Wes, who's our CEO. And that's really what sold me was his great, great conversation. I kind of liked the direction they were going. 

I like the stage that they were at. It was like I can bring some of the things that I've done to that team. I can make a big impact. I saw the growth opportunity there. But I still hold his head to this day. I think I mentioned it last week to him as I rub it in his face a little bit. I remember the interview process. I asked him and I said okay, so We're hiring like the first couple, AES. And then eventually, like, what's the plan that you're gonna have to have a VP, a head of sales, something like that, like, how long everything's unknown to the startup world. So he gave me some random timeline answers, like, we're not sure. So okay, well, when that time comes, do you think I have the opportunity to take that on? 

He's well, we could have that conversation when we get there. Like, you know, I don't know, sometimes you need some of that experience. And there was a very polite brush off to a candidate that they probably wanted to bring on, but didn't want to totally turn away. And so I am still rubbing his face to this day that I was like, That turned out funny, didn't it? I remember when he pulled me off when I asked that question. But how that conversation, like the opportunity, really connected with the team. 

So when I came in, we were pre product market fit, we barely had a product, I think about eight customers all like network connections, like people, the people that company to work for I was employed five or six. So the very first sales hire. So like the very first sales hire, they brought on a second AE a couple weeks later, I think he might have lasted three, three to six weeks before that wasn't a fit. And so just took it all on. So that's kind of how I found Woven it and landed an audit. The things that I liked were, I wasn't necessarily drawn to the product, or like, you know what we're doing. So I didn't know anything about software engineering, I had no idea about the actual challenges like that it was a challenge to go get into the market, can you figure out how to sell this thing, there's a lot of autonomy, I can create the processes, they didn't have a whole lot there to begin with. And they were gonna give me the opportunity to just go like I could live and die by whether I delivered results or not. 

I trust myself to go do that. I'll give it a shot. So what we do at Woven we deliver is we'd be bucketed into the category of assessments. We call them work simulations, and it's specifically for teams hiring software engineers. So when I started, we were very focused on early stage startups trying to hire you know, their first few engineers, small teams VPS underwater trying to hire but had to hire the headcount goals to get the product out. Over time now, we've shifted the product has definitely developed over that time. We are more focused on things like mid market, small enterprise, especially with the current environment where hiring is a little unstable. That's a more stable environment for us, and we help them to modernize and standardize their hiring process. For software engineers. 

It's a better candidate experience when they use Woven. It is also a better experience for the hiring team, they get a really strong signal on the candidates, they reduce the risk of Miss levels, or making that Miss hire, which can be critical, a fast growing tech company, and we alleviate a lot of the time that they have to take to evaluate those candidates by just putting the best candidates in front of them.

Grayson Faircloth:  22:52  

Yeah, I've heard that concept for sales hiring as well. Like Mark Roberge actually has a pretty cool like scoring system that he used at HubSpot around identifying good fit traits. So I'm super on board with that, I do that as well. So innovation with any new hire and stuff that, hey, they take certain assessments because there are characteristics that I want to hire for. So I love that. And you actually already touched on a little bit of this next question about, moving backwards in title, you brought it up in the interview. 

So you're obviously thinking about that leadership role? How did you plan to get there? Like, obviously, anyone can come in and say, hey, I want to progress in my career. I want to be a leader. How is it like, I am an AE now, but in a year, I'm going to be the director of sales, which sounded like it was your mentality coming in?

Ryan Ketchum:  23:40  

Yeah, some of it might just be like overconfidence in myself. I didn't necessarily have a plan to get there. There's so many things that change, but we were pre seed funding when I jumped on. So the first goal was like, Can we even be successful here, learn really quickly, and I was good with this. I was starting my own business on the risk that I could do all the things right, and we could not have product market fit, we could not figure it out fast enough, things might fail. So number one goal was to put up the numbers and show that I can develop these processes and that we can get this done because it's got to go past me if I'm ever going to get to a director or head of whatever the title might be. 

I'll also preface this with like, I'm not big on titles. I think there's a certain level of respect that I like from that. It's almost like this is how you know you've made it, it's the validation for what you've done. But I don't necessarily need a title with this. So I was okay with that. Now, I will also then come back and maybe contradict and say, being a little bit more mature now through the years in the startup world, but you always have to look out for your own career with this as well. And there is something to be said for having the right title, but we get the next step in your career knowing where you want to go. 

So you've got to kind of fight for yourself with this. So my overall plan was to be successful. And something I've always done, all through my career was take on a little bit more than what was expected of me or what you would normally do in a role. You know, as an AE, all I needed to do was generate my pipeline, close deals and drive revenue for the company. I'm also very money motivated. And again, some of it is like, once you get to a certain point and making money, like you need that amount of money you have that provides certain things for you. It is amazing like having no net money. 

When I started my first business, I lived above a garage in a friend's house and paid like $300 a month in rent, just to figure it out. Having money is way better than not having money. But you get to a certain point, it's like you have to figure out like, what does it really mean to you? How hard are you willing to work to get to, you know, from 100k, to 250k, to 500k. A lot of that is validation that says like you're doing a really good job, you're good at what you do. And that's something I pride myself on. I also just don't really like to be told what to do or like to have a boss. 

So the plan is always like figuring out how to make that happen. So I wanted to go put up numbers, and then I was always willing to fight for myself on it. At the point where we started to see some success in sales. The next logical step was, how do we get SDRs on board. And our initial plan with the company was the director demanded gen was going to hire and run the team of SDRs. I'm really vocal in what my thoughts are and why I think that way, and so I presented immediately, I think that's a mistake. 

Nothing against that person, the time, but they had never done cold calling, they had never done any management of SDRs, never been an SDR. And I said, you're gonna have a really hard time hiring the right people and training them up. If that person has never done this, we're setting them up and the SDRs is up for success. And they pushed back, still running with that plan. And what it ended up being was I was doing most of the training, doing most of the coaching, assisting with them on that, and what he did kind of some of the day to day management, and then quickly realized, like the path to success is like, let me manage that team of SDR. 

So I was doing that while I still had a title, then doing all the hiring and scaling that up. I don't even remember the timeline in which I took on a sales director or whatever, we'll build that up, we drove the pipeline enough that I could not handle all the deals anymore. So then we go to start to hire A's. That's when you start to move into the title. So a lot of it is just like taking on a little bit more. Don't worry about needing the title before you need to take these things to find out from whoever is your leadership. What are the projects that you can take on with that? How could you move the needle forward? Thinking two or three steps ahead in the business to figure out where you can make an impact? Where can you add value that sets you up to say, I'm the obvious choice for this? Like, there's no reason you wouldn't give me this. And I was always afraid, not afraid to fight for that title or fight for that next step up and tell them like I'm the person that you need to have in this role?

Grayson Faircloth:  27:59  

Yeah, no, I think probably a surprising amount of people don't actually like voices that are like, Hey, I guess asked in the first place. What else could we be doing? That would make me a good fit for this next role. I'm interested though, like, what you could have gone on you said you were motivated by money you could have gone on, just crushed it as an individual contributor got that nice a commission every time a new deal came in? Like what about you? Do you think you want to go into a leadership role? It seems like it was kind of natural. And you'd had plenty of leadership experience in the past. But what about you, do you think, led you into a leadership path versus crushing it as an individual contributor?

Ryan Ketchum:  28:40  

Yeah, listen, I had a lot of conversations, I was really lucky that he's open to having career conversations and figuring it out. And I struggled a long time with whether I wanted to just stay in this icy role and just crush it and cash my checks. And that's fine. I'm not worried about all these other things. Who do I want to step into this next bet? Some of it was that I liked the challenge. It got to a point I was doing really well today and then running some of the team things were cruising along, I was on track to like I was easily crushing what like my personal goals were for income. 

And that got kind of boring to me. At that point, I wasn't ready to really say I didn't feel like I wanted to step up until like a mid market or enterprise role. I really liked a faster sales cycle, things like that. And so this was really the next challenge and I wanted something that was going to push me and make me have to think through and also thought I had the skill set to do it. The other part is probably that little bit of a coach type of person that comes from the personal training background consulting background that I did, where I like to help elevate others with this like I'm probably going to do that either way. 

I want to be able to do this and I think it's a nice challenge and I've said this from day one I said you know I'm here for it. Let's get to our Series A like if I'm still the right fit and that's the right role. Let's It's a series B, we'll evaluate them. I don't know if I'm the right fit after that, or that's the next challenge that I want to go to either. And so it's always just thinking about, like, it's the challenge to go into it. And I do like, stepping back and like, I'm not afraid to roll up my sleeves, I'm not a leader, that's like not going to jump into a deal or help someone out with something or do the dirty work that you have to do in your day to day, but also really do like the strategic planning and the process and the thinking about how to make the overall system better, where other people can come in and succeed, as well. 

And then if they're succeeding, like, obviously, benefits you, which comes with this trade off is not everyone's always going to succeed or have that same drive that you do, and you just have to recalibrate what your expectations are for that.

Grayson Faircloth:  30:43  

Yeah. Something interesting that you called out. I've noticed that too, personally. So many people who are successful sales leaders do come from that coaching back, like how much of your time would you say goes into like, coaching versus like, the more like traditional management process systems like strategic thinking in like, how important do you think that coaching time is?

bottom of page