In this episode: Jason Witt, Director of Sales at Bonfire Interactive, shares the playbook for textbook career progression in sales. He answers – how can you make a career from doing what you love? What are the true differentiators between the roles of a BDR and an AE? And how can you separate yourself from your peers with a growth mindset? Listen for all that and more!
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In this episode: Jason Witt, Director of Sales at Bonfire Interactive, shares the playbook for textbook career progression in sales and answers on making a career from doing what you love, etc.
Joseph Fung: Today we’re speaking with Jason Witt, the Director of Sales at Bonfire, and you’re going to hear an interesting story about how he went from pursuing a CFA to pivoting into sales with tons of ups and downs, including completely crashing and burning in his first demo. This is gonna be a fun conversation. Stay tuned!
Welcome to sellers journey, the podcast where we speak to great sales reps and leaders and share their real stories from start to sales success.
Joseph Fung: Hey! Jason, thank you so much for joining us today. How are you doing?
Jason Witt: I’m doing good, Joseph. Thanks for having me.
Joseph Fung: Fantastic, so our guests, our audience, would have heard your introduction. And I’m so looking forward to getting just some of these stories. But to start off at the beginning, maybe can help our audience that, where’d you go to school? What were you studying?
Jason Witt: Yes, so born and raised in Waterloo went to Wilfred Laurier as well. Did economics and Finance as my undergrad there.
Joseph Fung: Nice, and now you’re Director of Sales what’s the elevator pitch for Bonfire? Well, what does the company do?
Jason Witt: Yeah, you know, happy to kind of enlighten you here. So it’s a really, Bonfire is about reinventing procurement to better our actual world. So our whole thought and philosophy is that if you can spend smarter in the public sector, that means more resources, better services for us as a population in society. And you know, given kind of, the situation out there, I think, it’s more prevalent than ever.
Joseph Fung: Totally fair, and I love the attention and a characterization of what’s going on today. I imagine you’re seeing a shift in your selling processes. How’s that impacting your sales cycles?
Jason Witt: Yea, you know it’s been it’s been interesting. We actually to just help out, we decided to at the beginning of this whole crisis start offering Bonfire for free, and it’s actually just been a great gateway just to having great conversations with people helping where we can, some people are leveraging the free program, other people from that free program or back we decided to be clients already. So for us it’s been an interesting pivot as we’d never offered you know free services before, but you know we’re learning and it’s been it’s been good we’re happy to be helping people and at least the public sector and just in general across Canada, in the U.S.
Joseph Fung: So, what is the hard price to beat? Is it changing your sales cycle and sales motions much?
Jason Witt: It’s just, I think, a new pathway to it. It’s maybe delaying the cycle a little bit. But we’re finding that it’s starting to generate a more humanistic approach to selling. So you build that relationship quicker with the prospect, and we’re actually seeing kind of conversion rates, trending upwards, because you have you know that that ability to just get you know one-to-one with that prospect to understand what the pains that they’re dealing with. Especially pains that are prevalent right now and offering something for free to help them. I think it has really allowed them to look at us different than just, you know, tech salespeople but actually people that generally want to help them.
Joseph Fung: You know we can spend a ton of time talking about what you and your team are seeing. But I want to make sure that we hit on some of the things that we spoke about in that intro. You weren’t intended to be a Director Sales, that when you started. You shared a great comment about you know even the influence of your father had on your direction. Maybe you can start us off there. What was your original plan?
Jason Witt: Yeah, for sure, yeah, so I had taken the same kind of program that my dad had done in University. He’s a CFO for an investment firm. And he did his, now CPA, but back in the day was his CMA, and so I decided I kind of want to do my CFA. My now wife at that time was in Toronto doing some co-op placements as a graphic design and had a job lined up there. I was working for TD. So you know our whole idea was to be big city people, and you know myself working on Bay Street and my wife do graphic design therefore for a firm, and she actually got a job then instead in Stratford for a boutique firm there. And completely kind of pivoted the way I was thinking of our future. And so I wanted to look at something look close to home because I hated that commute.
Joseph Fung: Now, your role in the bank. Can you share a little bit about how you got started there? And what that was like?
Jason Witt: Yeah, so that was actually my first job kind of coming out of University that was just more in the Finance and kind of business field. So the idea was, you know, get in at one of the local branches here, and then I’d build some connections with the Branch Manager. And they had contacts kind of down on Bay Street, and I thought I’d be going into kind of financial operations and analytics and analysis and all that fun stuff. But yeah, an interesting kind of story. So my dad kind of sat down with me we shared a glass of wine one day. And we were you know talking about well, do I go to Toronto? Do I stay here? What do I do? And he kind of, you know, laid it out of what he had gone through. And you know the gruelling 70-80 hours of work as an Associate pretty much for 10 or 15 years until you kind of get into the role where you start reaping the rewards. And I just at that point in time, you know at 25 years old, you’re kind of thinking to yourself there’s got to be an easier way.
Joseph Fung: It’s kind of solved your own task!
Jason Witt: Yea to kind of to make that you know, same kind of money and in your life and achieve those kinds of things. But maybe do so here in Waterloo, and so I kind of looked at what was booming in Waterloo, and I knew tech was and I looked at sales and I was always kind of a personal person and you know in university, I had odd sales jobs. So I’d been like a fundraiser for Sick Kids Hospital and even like did demos for cure eggs at like future shop and Best Buy stores back in the day. And so from there, kind of just looked at what Waterloo kind of held as an opportunity and tech in my mind was just ever-growing and when you look at what’s really like a job in sales, it’s I think never gonna die that’s tech sales. And that there’s always going to be someone that needs to technology regardless of what that technology is. And so that’s kind of what led me to pivot from, you know, for pursuing the CFA pathway to now a Sales Director.
Joseph Fung: So you’ve got the degree you were kind of a CFA, you’ve got a role in a bank, you’ve got a father with all these pressures. What anxieties or uncertainties did you have as you looked at a tech sales role? Because there’s a big gamble there. And I’m sure it wasn’t just kind of an easy decision. You know what was weighing on you?
Jason Witt: No, for sure! It was even the fact of like cold calling. Like that when I walked into kind of that first interview as a BDR, and you know that was with the desire to learn. You know they talked me through the daily responsibilities, and even cold calling like that is even for people that are very outgoing. You know it’s a difficult thing to do. So I always give so much credit to BDR’s wherever I am or whatever role I’m in because they are front lines, they’re calling people, they’re there that first line of trying to pitch what this company can do for them. And so you know that that was probably a nerve-wracking thing for me was.
Actually getting on the phones, making the dials, but you know I just kind of pushed through it and after you do it and you get you know about a hundred no’s sent your way five hundred no’s sent your way, it just kind of rolls off your back and then you realize that you know what these people kind of think of you or a saying or whatever you know it doesn’t really kind of impact you or affect you too much. So you know, once I got over that hurdle and realized that what we were doing was great and an offering was great.
Then I was just finding the people that cared about what you cared about. And then when you had that connection, that’s when I really started to love my job, is when I could talk to those people that cared about what we cared about. and you could see you know things clicking there and so, I think that was how I overcame something that was very nervous for me, and I think nervous for a lot of BDR’s but what you have to look for in that future is just really just finding what makes you comfortable in that role but then capitalizing it and using it to advance your career forward.
Joseph Fung: I love the way you phrase that, open about the anxiety, the uncertainty, the fact people say things. But finding people and speaking with people who care about what you care about. I think it’s a fantastic way to a phrase. Thank you for phrasing it that way.
Jason Witt: Oh yeah! No problem!
Joseph Fung: That role you haven’t really interesting leap we hear from a lot of people that they can get into that BDR role. But often, where they hit a bit of a plateau or a challenge is transitioning from that BDR to an Account Executive role. Because some companies make that easier, some companies make that harder. And it’s always a challenge! You had the added complexity of going from a very successful scale-up, that’s known around the world to a relatively anonymous startup. Can you share a little bit about that leap from BDR to Account Executive? Because that story is a lot of fun. I’d love to hear near words.
Jason Witt: Yeah, no problem! It was it was interesting. There was a BDR that I’d given advice to. Even in an elevator at D2L and he ended up getting hired. And you know he knew quick flatter and CEO, and he had actually said because I was looking to kind of do that transition he said, “hey, I know this startup, they’re doing really cool things, they were just coming back from wide Combinator at that time”, so the big incubator down in Silicon Valley. And he said you know, “I can be in connection and just go in and chat with these guys”.
And I was looking at Vidyard as well and a few other organizations in addition to kind of where I was at D2L and then from there, I sat down with the guys, and it was, I still remember coming into that first interview, that was on location we’d met at Balzac’s of course and then, the second interview was actually at this pool shop so Acapulco pools on Victoria they had kind of leased out the front of the pool shop, so when I got in there you know I’m all in a suit and a tie and all the other guys are in jeans and t-shirts and flip-flops. And I hear a band saw going behind because it was still an active construction shop behind us. So there’s this band saw going and …
Joseph Fung: Is this the place with the Bojangles Dance studio right next door?
Jason Witt: Yes, right!
Joseph Fung: You got a pool shop on one side and a dance studio on the other, but you’re gonna sell tech. Okay, I got it so far! So we got six guys there at the front of the shop.
Jason Witt: So then the second interview is kind of mine all VP you know he was a director then and he was selling, and you know they took me through a demo of the product and it just kind of it clicked you know they kind of pitched me what Bonfire was trying to do, and where they’d come from, and I loved that you know they had gone down to Silicon Valley done really well in wide combinatory and they decided to come back home and came back to Canada and tried to make a footprint here.
But then you know I just got behind the story. So then ended up taking a rep role there, and I still kind of remember the first day walking in and doing my thing and kind of at the end of the day there’s a nice seasoned sales veteran, and you know it was kind of his three-month probation, and they had decided to part ways with him, and you know it’s coming from a BDR and now I’m the only rep there, and I’d never sold anything in my life you know the fear just set in. I remember calling my dad in the car just telling of this, and she just laughed, and he said, “Well, you better buckle down for the next three months”. And exactly, I did!
Joseph Fung: Sympathetic! I love it! So I gotta ask. They must have given you some indication as to why they walked out an experienced rep but kept you in the seat at the end of day one. You know what do you think you brought to the table that caught their interest and gave them confidence in you?
Jason Witt: Yeah, so this was actually a funny story. So I actually didn’t find out why they kept me until kind of years later we were at our annual Christmas party. I was just, you know, talking to my VP and CEO and Kory and Andrew and I just kind of said, “Listen, guys! Like, you put me in just such a weird position like what happen? Like walk me through like, what were you guys thinking there?”, and they finally kind of laid it out for me to understand. And it was a pretty nice thing to hear from them. You know they had said that the day you started, you came in, and you just got to work, you started developing your territory, started identifying Top accounts, you even started calling people, and we weren’t even expecting that.
You were trying to elevator pitch Bonfire, and you barely knew Bonfire. But it was just, they had kind of said, “in 24 hours, you had kind of put in more effort to try and further the company then”, you know kind of what one of these seasoned reps had done. And so that was, you know, all of a sudden, they had sat down, you know, 30 minutes before they had met with this other guy and just made the decision. And they, of course, are laughing the entire time while they’re telling me this. and I’m kind of providing the other you know yin to the yang of, yeah, well you know the way to kind of put me in the hot seat and you know it was, it’s been fun ever since. So it’s been a blast!
Joseph Fung: We talk a lot about how startups, you know the only constant is changed. You got to live that with a front-row seat. Congratulations on making it through it. Wow, that must been terrifying!
Jason Witt: Yeah it’s been an experience it’s been kind of everything from early days you know the company’s six little, the company in back then with six guys and I sitting down saying, “Okay! Well, we need to hit this revenue target, or we, are we gonna be able to pay the salaries or the bills you know next month? And so what are we gonna do to do this?”. Luckily it’s not a problem anymore, but you know now there’s just bigger numbers to go after with other problems tied to it. But it’s then it’s been really interesting.
I think that’s one of my favorite things, at least in my role there and how I’ve developed and transitioned from a BDR, kind of the role I am now, is doing so in a startup and a company that had to reinvent and develop as well. So that was just a really cool thing was it added an extra layer of complexity, which ultimately, I think, kind of drove me as a rep to just work harder and try and think more outside the box because you didn’t have all the resources that you have. You know, at a company that has been around forever and has a solid sales team and you know knows the playbooks inside and out. It was something that we all had to learn. And I think that’s an experience a hundred percent wouldn’t change for the world and would highly recommend to anyone who’s got the opportunity to do it.
Joseph Fung: So it’s just kind of the other bookend. You started as a BDR, six people, it’s less than five years later you’re the Director of Sales. I think is Bonfire now.
Jason Witt: We’re about a hundred employees.
Joseph Fung: Okay, now, so let’s just kind of for our audience, keeping that in mind. So you’re Jason has had the chance to go through four or five different roles in less than five years of incredible growth. So you know I say this loving startups. But often, in the early days, it’s chaotic. And we have no idea what we’re doing. Can you share a little bit around an early demo that was maybe a good example of that? And you spoke about how it was a complete disaster, your first demo. Can you share that experience a little bit? I think that’ll be a great experience for the audience to hear.
Jason Witt: Yea, for sure! So this was, in my first week of being there as a rep, they decided after you know the other rep leaving, I had to take on some of his demos in addition to my director.
Joseph Fung: Totally…
Jason Witt: And so they kind of said listen you know listen, Jay, we, you know this is a bit awkward and tough, but can you lead this demo. It’s on Friday, and I started on Tuesday. So in three days, you know I’m trying to learn the product, I’m trying to listen to how my now VPO was demoing it and selling it and all the nuances. And I had to learn even like what an RFP was. And you know how do these public agencies even purchase things? And so it wasn’t even just learning the tool, but how did these agencies even purchase? And what are the policies? And how does this affect it kind of by state regulation? And so there’s just so many things that I kind of thought I knew and I went walked in, and I started demoing, and about 30 minutes into this hour-long demo, the prospect kindly stops me and just says you know what I think that I’ve seen enough this really doesn’t look like it’s something for me.
I’m gonna get going, and so that was the first day. Luckily I was leading it by myself because Andrew was on another demo, and you know I was in this little calm closet that we had, which was our janitorial closet. So you know no one had really heard this, but you know that that was kind of my first selling experience as a rep was, just someone stopping me and saying, “no, thank you! And go from there you’re just kind of demoralized for the next 10 min of it like, how am I gonna do this? But you know you learn from when he and just push through it, and you know since then I’ve probably led thousands of Bonfire demos. But you know, the fun story is it account kind of turned back around, and we actually got the account back about you later, and you know it, it all comes back around, so I think that’s just a great thing.
Joseph Fung: It does. I mean, having somebody walk out in the middle of the demo is almost worse than just having a no-show that’s tough. Kudos to you to stick with it, that’s a tough first week. Wow, this is incredible. I think about the testament to your work, turning it around. I mean, you had some rough challenges at the beginning and now as you’ve grown to be a Director Of Sales there. I think that’s a huge testament to your work. So congratulations. You know, great work, Jason.
Jason Witt: Thanks, Joseph!
Joseph Fung: It’s also a testament to Bonfire. I think they’ve got a great founding culture if they can give somebody that kind of an opportunity. You know, let them stumble and still see great success. I think that’s a great example of a kind of living and breathing that agile startup life. You know, kudos to the whole Bonfire to you. I know, I said, I won’t take you too long. Do you have time for just a couple of rapid-fire questions before we wrap up?
Jason Witt: Yeah, of course!
Joseph Fung: Perfect! Okay, so you’ve been at Bonfire, you’ve been at a bank, you’ve been, had a desire to learn. Tools! What’s your favorite sales tool?
Jason Witt: Half it would have to be Gong. That’s my favorite sales tool right now!
Joseph Fung: Nice and outside of work, Entertainment. What about movies? What’s your favorite movie?
Jason Witt: I was always a big fan ever growing up of just the James Bond franchise. So anything 007.
Joseph Fung: I love it! Okay, last one. You shared what your objectives were kind of going through school and graduating. But casting your mind back even before. When you were a kid, what did you want to go up to be?
Jason Witt: Well, with 007 and watching those movies along with my grandfather. I just thought that I was going to be a spy and work for, you know, the Canadian government and traveling all over and that and spying on fun villains but at last that that just was not a real job that was available.
Joseph Fung: Director Of Sales is a close second. I gotta say, though!
Jason Witt: Hey, you get your travel, you get to travel!
Joseph Fung: There you go. Jason, this has been such a delight. Thank you for making the time and for sharing your story. I enjoyed this conversation so much.
Jason Witt: Well, thanks for having me. I appreciate the opportunity. It was great to tell it.
Joseph Fung: My pleasure. Looking forward to our next conversation. I hope you have an awesome day.
Jason Witt: Thanks, Joseph.