In this episode: Kenny Goldman, Co-Founder of Kicksaw and Sprintlio, joins us to share his journey from individual contributor to tech founder. How do you look at risk-taking depending on your career stage? How do you balance the effort needed to achieve your desired goals? How can you grow your network in sales outside of your 9-5? All the and more next!
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In this episode: Kenny Goldman, Co-Founder of Kicksaw and Sprintlio, shares his journey from individual contributor to Tech Founder. How do you look at risk-taking depending on your career stage? All that and more next!
Joseph Fung: Today, I’ll be speaking with Kenny Goldman, the Co-Founder at Kicksaw and Founder and Host of Sales, to one of the largest recurring sales meetups in North America. Kenny is not only an amazing Community Capitalist, but he also has the unique perspective of having landed all three of his sales jobs via Twitter. You’re really going to enjoy this conversation.
Welcome to seller’s journey, the podcast where we speak to great sales reps and leaders and share their real stories from start to sale success.
Joseph Fung: Hi, everyone, I’m Joseph Fung. And today we’re chatting with Kenny Goldman. Kenny, how are you?
Kenny Goldman: I’m doing well its a beautiful morning, and I’m looking forward to being on the podcast today
Joseph Fung: Likewise. You have such a fun journey, and I know we’ve chatted so many times at sales to I’m so glad to get the chance to dig into details. Thank you for joining us
Kenny Goldman: Of course. Thanks for having me.
Joseph Fung: So started off Co-Founder at Kicksaw, I know you’ve worked with a ton of companies that are absolutely incredible, but maybe you start off by helping our audience. What does Kicksaw do? What’s the elevator pitch?
Kenny Goldman: Sure it’s super simple. We are fraction yet fractional sales or revenue Ops. So we come into companies, help them either at depending on the stage they’re at stand up and build the fundamental aspects of their sales and revenue ops functions or go into an existing teams and help augment and elevate their existing processes in tech stack to support the continued scale or growth of that organization.
Joseph Fung: That sounds like you’ve got some high-stakes responsibilities there. How do you balance that with your work of hosting and running sales to you?
Kenny Goldman: The good news is you surround yourself with great people and a lot of the times the work itself doesn’t necessarily fall on you. so and been fortunate to work with the team over at Tectia which is you know, another meet-up and they’ve been growing tremendously here in Toronto and partnered with them four years ago to help oversee a lot of the background aspects of the sales deal. Things like volunteers, venues, ordering food, some of the sponsorship conversations, volunteer, oh I said volunteers and other administrative aspects, and that’s given me the ability to focus solely on speakers and content, the things that I enjoy the most.
Joseph Fung: Now I want to get back to this topic of the speakers and the ecosystem. Because I think there’s some really good subject, subject matter to dig into. But we do try to focus on people’s stories, so maybe we can rewind, you know, back to the earlier days in your career. Could you start off? Where where’d you go to school? And maybe you could start off by sharing a little bit around how you landed your first job? Because your first role at Vidyard, there is such an interesting story. So maybe you can help us out with that.
Kenny Goldman: Sure yeah, so to school at Wilfred Laurier, University out in Waterloo Kitchener. But before my first job at Vidyard, I actually started working when I was a teenager at a Telemarketing Gig. So, I was making you know your hundreds of calls a day, trying to sell people windows and doors. When I was as young as 13 years old, is that legal I don’t know. But that that helped me develop some thick skin because 99.99 percent of the time you’re getting rejected. And so you kind of get used to rejection I think that was my first entrance really into sales trying to convince someone over the phone to have someone that they don’t know visit their house to inspect their windows and doors. Not easy to do. Especially someone that is just past puberty and probably doesn’t have doesn’t sound much like an adult.
Joseph Fung: So how did that go? How did you do in that role?
Kenny Goldman: You know it more than anything I think I developed responsibility at such a young age. You know you have a shift you start at 6 pm you work till 9-9 30 P.M on weekends and weekdays. And so sorry weekdays only and then weekends you’d work from like at 9 00 am to you know 2 pm type shift. And very few 13, 14, 15, year olds are doing that. and I did it with a couple friends so made life a little bit easier and actually found different jobs, I applied to newer ones, more modern ones, more sophisticated ones that had better tools and better management and it was kind of my first foray into having a responsibility, having a job, earning some sort of income, depositing that and managing my own money and so I developed a lot of skills early on that way. And it felt good to be in control of the money. I made right and being able to spend money at such a young age on things that I wanted, rather than have to focus on money for my parents or you know birthday money or things like that.
Joseph Fung: Nice.
Kenny Goldman: So that was good. And then from there i actually moved into a Retail Gig at a company called The Running Room, if anyone’s familiar with The Running Room. They sell running apparel and food everything devoted to athletes primarily runners and walkers. and managed you know the opening of the store and was just very active at that store and once again that gave me experience selling being in front of people talking to them, educating them and just developing that skill set of how to hold a conversation. How to engage people, how to present different things like you know new apparel, new shoes, how to explain things in a way that appealed to their interests. And then finally I went to Laurier for business Bachelor Administration, concentrated in entrepreneurship. And the way I got into Vidyard was I was always eager to just find a job, get a job. I always felt that like maintaining a job was I guess the best practice or conventional at the time you know wasn’t because very few people I knew had a job in the third year of university. But I found on twitter that Vidyard was hosting a recruiting event unbeknownst to me it was solely an engineering recruiting event like you walked in the door and to the right and there’s a coding test and it was primarily engineers there and they’re you know they’re just focused on engineers right as a lot of early stage companies are. but I walked in there being the only sales person, slash marketing person there, walked right up to Mike, I said, hey mike you don’t know me, but I found this event. Here’s my you know here’s my resume; I’m interested in working for you. And I think he was so shocked. I don’t think he knew what to say at that time because what’s he says that, a burger of university can’t even work full-time doing it an engineering event. So he introduced me to one of their only sales roles at the company, Dan Wardle to chat with me. And I almost think out of out of guilt they brought me in for an interview.
Joseph Fung: So to make sure that I get this right you go to the engineering recruiting event, walk up to the CEO, tell him you want to work for him and they feel guilty enough that they give you an interview. Is this right?
Kenny Goldman: Pretty much. It was it was naive you know naivety at its best. Right. Not knowing what was going on, but just doing it. Being a go-getter. and so landed me that interview and they initially said, no Mike’s, like I have you know no use for a kid who’s in school, who can’t even work here full-time, you know you’d be part-time. You don’t even know what days you’re available because you don’t know what classes you’re in next semester. So how addicts would be to hire, you so I finally said, I’ll do it for free, so no laptop, I brought my own Sony laptop, clunky Sony laptop, and I came to the office almost as much as I could, I skipped classes and I was trying to be there full time every single day for three months until finally I was actually you know doing work, I was converting leads, I was you know reaching out to inbounds as quick as I could in class, sending someone an email as I saw they came through salesforce that you know they appreciated my hustle they liked the fact that I want to work hard and had a work ethic and offered me the co-op role for that summer and so then I became actually full-time paid in a role at Vidyard after that three-month free stint.
Joseph Fung: Okay, so a couple of couple of questions. First off you mentioned how you came across this meetup. Is that where twitter kind of falls into the story of landing your role at Vidyard?
Kenny Goldman: Exactly, yeah I had no idea who Vidyard was, until I saw them being active on twitter and Mike was active on twitter and so that that was the introduction to Vidyard at the time for me.
Joseph Fung: Okay so now I can get a better idea of this image. You’ve got this kind of university student, learns about the startup you know on twitter attends the event, convinces them to bring them on. What did they have you do? I’m trying to imagine myself in the role of you know having somebody with so much you know moxie and driving the enthusiasm, and I confess I don’t know what I would have them do in that role. What did they have you working on?
Kenny Goldman: Yeah I think at that time for Vidyard it was just prospect as much as you possibly can.
Joseph Fung: Wow!
Kenny Goldman: And they had lists upon lists of you know going to different events and people that they haven’t touched base with or people that have signed up a while back that you know went cold. So they had thousands of people in lists in Salesforce who were just not even being nurtured but they were just sitting there cold. so just started going through that list and started sending emails and touching a hundred people a day and you know is a good opportunity for me to learn how to send emails, sometimes people would say, sure give me a call, and I’d have to call them and pitch the product and pitch you know who Vidyard was. And so it’s a really good introduction into learning everything i possibly could about the company about what they do, about why Vidyard was unique in the market, who the competitors were. And none of that was provided to me, it was very much, ask a million questions or do a ton of research online to find those answers because everyone was wearing multiple hats at the time. You know to put this in perspective, I was there’s that at if had I been a full-time employee that would have been employee number like 14.
Joseph Fung: Wow. That was very early.
Kenny Goldman: So it was a very small team. Yeah, it was you know since you’re familiar with them it was when they moved out of the Greenhouse into their first kind of office. Literally a month after they moved from the Greenhouse.
Joseph Fung: And that’s an exciting time. That’s a good point in their history.
Kenny Goldman: Very fun yeah, yeah the team it was it was exciting to be around them at that time.
Joseph Fung: Yeah it’s clear at that time not beyond just the fun, you learned a lot. And this is a great story of a first role while you’re at school, you had graduated before you landed your role and hired though right?
Kenny Goldman: Correct, yeah so what I did was work for free for a few months did my co-op in the summer and then what I presented to Mike, and the CEO was that not exactly the end but, near the end of my co-op stint. What I’d done is, I’d actually moved all my courses to either online courses or evening courses, 6 or 7 to 9 pm or 9:30. And I pitched the concept of a full-time role with Mike, to Mike performed then in my co-op and kind of present my schedule and said I can already commit to a full-time gig. And I’ve been doing well my co-op. so we went forward. so my fourth year of university, I was working full-time at Vidyard and full-time at school with the exception of, I think Fridays was the only day I had to have a class at like 2 to 5, so I’d leave half day on Friday and then pick up the slack over the weekend, responding to emails or prepping emails for Monday, otherwise I was there full time, Monday to Thursday 7 30 till 5, 6 pm as late as I could possibly stay before I had to go to class.
Joseph Fung: That’s a crazy workload. I’m impressed, that’s a ton of work,
Kenny Goldman: It was ironically my best year, I think being so busy required me to go active, prepare not waste any moment I had. So it was actually my best performing year in school. And I had an amazing time and learned a lot at Vidyard.
Joseph Fung: I can imagine how the time management skills that you pick up as a sales rep helped out in the schooling as well. So yeah I can imagine that there you go.
Kenny Goldman: Yeah so I was there just to finish up my time of video and I was there I graduated and then I stuck around Vidyard for I think another eight or ten months. And just learned a lot and met a lot of amazing people, before I took the leap to hired.
Joseph Fung: Now you mentioned how you landed your role at hired as well as that helpful via twitter. Maybe you could share those stories. You know how did how did those opportunities come to be?
Kenny Goldman: Yeah, I actually landed a ton of opportunities through twitter. A very interesting one that not many people knows is there’s a guy by the name of Heaton Shaw, he was one of the co-founders of Kissmetrics. He’s you know pretty influential in San Francisco. And just a product marketer growth marketer and he just write a lot of great content. And you know there was more of a lurker on twitter than anything. But one time he posted the need for some help doing a research project. and I just happened to respond to him faster than anyone on twitter that day and he brought me in and we did a post on, this slack have product market fit back in 2015. When stock was really just try end. I got to develop a really good relationship with Heaton and a few other people and you can find it on that online just go to Heaton Shaw slack research project and basically, we distributed a type form survey or was it survey monkey to 8-900 people. Through his connections and what very little connections I had around people’s thoughts and in product market fit of slack. And then I compiled all the research presented all the responses to him and then he wrote it up with a content marketer. So that was amazing opportunity for me to see how a lot of that stuff is done and work with someone who’s brilliant. And that was solely through twitter. and he’s been invaluable resource and friend as I’ve kind of built my career and presented ideas to him and picked his brain and anytime I visit San Francisco he’s always a good person to connect with. But through Hired, I noticed that one of the early employees a guy by the name of Andre Cherub, who comes from Canada initially was looking to open the Toronto office in the Canadian presence of hired. and so he was active on twitter posting it posting the roles and once again naively the role was for the good GM, and I’m like I’m no GM but I know the Toronto market pretty well and I know people and I know startups and you know I think I think I can add value to this company. So I applied and I think once again he liked my tenacity and I reached out to him email, twitter any possible way to get in touch with him. I did so and finally got a response. And went through the actual formal interview process. And landed the first sales role that they hired in Canada.
Joseph Fung: That’s fantastic. So yeah you’ve worked in some dare, I say kind of titans in the tech, in the sales tech space, I mean Heaton, Michael, Andre all remarkable people. And you get the chance to run this incredible meet up event. So maybe we can kind of step a little bit from just the individual roles for a brief moment and touch briefly on the meet up itself. You also spoke about bringing in speakers from out of town. Can you share a bit about why that’s so important? And also just how do you make it happen?
Kenny Goldman: Yeah, so sales to for me was at the time an opportunity for me to develop my public speaking skills. Very few people cared about what Kenny Goldman had to say. And even today right it’s what are a lot of the practitioners doing out there. But at the time I had no platform of which to speak from and I felt that I lacked that that skill. So I figured if I could bring together a smart reputable panel of speakers in the sales community, which I know, then I’ll be able to be on stage beside them and have some format to present or talk to people. Yeah and so that was kind of the impetus for sales TO. There was of course a lack of you know a sales community and a presence in Toronto. But more than that for me it was just an opportunity to build my network meet some people have an excuse to reach out to some awesome sales leaders. And be in front of a audience which i can you know practice speaking. so that was the initial thought process around sales TO and initially it was not about finding people abroad, it was around great, let’s collect connect the local talent, let’s expose some amazing thought leaders and influencers and let’s present new ideas and concepts to people who are up and coming in their careers or who’ve been in sales for a while who haven’t you know haven’t been improving to some of the more modern principles and concepts and technologies and whatnot.
Joseph Fung: So that pattern of continuous development, it’s been so prevalent in your journey there from your world of Vidyard, you said launching sales to you, to learn and build your own public speaking skills. If we were to reflect that back to a broader audience, you know people that are trying to build their own careers now what would be some of the areas that you commonly see deficiencies? Or another way to put it you speak to so many sales reps, where are the patterns of gaps? So where could people differentiate themselves in today’s market?
Kenny Goldman: Yeah I think the resources are all available I think it just requires the willpower and desire to do it. There’s so many books out there that talk about a lot of amazing concepts that help people in sales. it has nothing to do with sales itself, but it has to do with talking to people, presenting ideas, sharing thoughts, helping people open up, and these all relate to sales but they’re not directly or only a sales concept or principle like, Influence by Robert Cialdini, is a great book that talks about you know those types of concepts in psychology and getting people to talk. The Mom Test is another great example of a book where it teaches you how to present ideas in an unbiased manner, right. You love your product, you love what you sell, but not everyone does, most people don’t actually. So how are you able to communicate you know the value prop and concepts of what you’re selling in a way that doesn’t sound like you’re pitching. Then of course, there’s all the amazing sales books out there too. That I’ve read but I think you know number one is there’s a ton of resources out there that can help people improve their abilities and their grammar and concepts to use that I think don’t many people don’t take advantage of.
Joseph Fung: Now, I love how you started off by mentioning how these aren’t necessarily sales specific skills, they’re about other areas. But also in another conversation we actually spoke about the importance of sales skills, like that background, the mindset in founding and running a company. So for those people in a sales role who are looking at tech companies, maybe you can expand on that a little bit, why is it so critical to the success of a company?
Kenny Goldman: Yeah, I think a lot of the success of the company is getting out in front of the right people and how you get in front of the right people? And how you get them to respond? And how you get them to engage in a conversation? Is going to open up a lot of doors for you to learn about what you’re building, about your market, about what people think about what you’re building, and so you know first and foremost is you’re solving a problem at a tech company oftentimes. from you’ve experienced a problem, you know someone, someone else’s experience and you often have a ton of different hypotheses around how people react, how people act, how people experience those pain points, how valuable are solving those pain points and the only way to really test them is talk to people early on. Right. It takes time to build a product, it takes time to get something out of the market, I think it’s so important that you develop the skills needed to be able to talk to people outside of your immediate circle your network. How to find people, how to prospect, how to reach out, how to communicate your thoughts, how to incite some sort of curiosity out of someone and be able to relate and resonate with some of their pains in their problems. And those skills I think help propel and accelerate the early phases of a company to get to a point where you can get early users or early customers and actually use that as leverage to you know hit critical mass inside of a market. Obviously, I’m oversimplifying things and skipping things but I think you know product will get you pretty far certainly. But I think at the end of the day you have to back that up with discussions and research and in conversations and relationships.
Joseph Fung: I love the thought. And I love how deliberate you are about not just your own improvement but you know the way you guide people to that that ongoing sense of improvement. If we could pasteurize forward for a little bit, what are you working on next? You know if I dare ask what area of your own work or your own business are you working on improving next?
Kenny Goldman: Yeah so I’ve I recently read a book, oh it’s escaping my mind, in The Negotiation book, by Chris Foss. That was it. He was a former never split the difference, from our negotiator. And a lot of what I’m working on is learning how to present or sell services. My business is a services business, we don’t have a product. We don’t have the same scalability as a product and there’s this negative connotation that people have with services business or with consultants in general. And understanding how to address a lot of those objections or those negative initial impressions or perceptions of services or consultants is something that I’m focused on. Furthermore, I’m also focused on another aspect of sales which is less selling to new users or new customers and focusing on existing customers. a lot of our businesses consultants is the ongoing relationship we have with people and how do you maintain that relationship, how do you strengthen that relationship and how do you build that rapport as quick as possible because the more you develop a relationship we all know that people buy through emotions, the better likelihood that they’ll want us to continue to support them work with them and continue to add that value but if they don’t like us, as humans as partners then the likelihood that they’ll continue to speak up speak up about their problems or where we can help out. You know it we won’t get those opportunities as much.
Joseph Fung: Kenny, this is remarkable. I know that I promised we wouldn’t take up too much time. You okay if we go through a couple of really quick questions, the rapid fires before we wrap up?
Kenny Goldman: Let’s do it.
Joseph Fung: Okay, so first off, just some contact information, you are incredibly well connected and you’ve got some great thoughts if people want to reach out to you or to Kicksaw, where would they find you?
Kenny Goldman: Twitter, LinkedIn. Very active on either of those, easy to find, Kenny Goldman. So it’s probably a good starting place to get in touch with me.
Joseph Fung: Awesome. And if people are interested in learning more about sales TO and coming out to these incredible meetups, where would they learn more?
Kenny Goldman: salesto.org has all the information you need. There I’ll of course always post it on Twitter and LinkedIn as well. So many of my posts are related to upcoming events or speakers things of that nature. So you can easily find any information on my on the site or through my social handles.
Joseph Fung: And I’ll make sure we grab those links and put them into the description of this episode. So if you’re listening in check out the description of the episode to find those links that Kenny shared. A couple of rapid fire questions and then we can let you get back to all the fantastic work. Tools. Everybody’s always curious about tools. What is your favorite sales tool?
Kenny Goldman: It’s a good question. We’re not your typical SAS Company, where we’re inundated with tools and using every single tool, we’re actually trying to limit the amount of tools, we use until we validate it and use the right tools but we are using a few tools. And recently I’ve been spending some a lot more time in Gong, only because I can’t be on every single call that we have with customers. And I think it’s so valuable to give feedback and to hear how other team members are performing. and so I use that is any opportunity I get to listen, rather than a podcast or music, I’ll try to listen to some Gong calls to see where there’s opportunities for us to improve and everything is always easier in hindsight. Right. So as I’m listening to things I can pause and take time to take some notes or re-listen to certain portions of the call. but right now I’m spending a lot of my time inside of Gong, being able to, I think it’s like nuggets of gold, is the way I’m phrasing it, in being able to identify areas that you know one person may have struggled in or a complicated question that now, I can present to the whole team and everyone knows how to address it and feel comfortable with that type of question.
Joseph Fung: That’s fantastic. That’s such a great recommendation especially given all the attention to continuous improvement. So, thank you.
Kenny Goldman: Of course.
Joseph Fung: Outside of work though, I know that we’re not going to the theaters very much while everyone’s working from home, but what’s your favorite movie overall?
Kenny Goldman: Yeah I think my favorite movie is, I’ve always had an affinity towards ‘Forrest Gump’, love the movie I love Tom Hanks. I think many people love the movie, it’s a fantastic movie, but always just love that movie and anytime I see on TV, I can happily re-watch it at this point I’ve seen it many more times than I can count. But that’s fantastic maybe.
Joseph Fung: And then casting your mind back to your youngest years, when you were a kid, what did you want to grow up to be?
Kenny Goldman: I don’t think I had any crazy aspirations. To be honest, I’ve always been very interested in psychology and helping people think through problems and helping understand their problems. So that’s always very much appealed to me. Something that I’ve always wanted an area of interest I wanted to get into. So psychology has been something that that probably as a kid at the time, I didn’t know what psychology was, but working with people and helping people to think through some problems or areas of uncertainty and just communicating with people. I love any interaction i get with an individual or someone that I know or don’t know. Always energized, always feeling good at the end of it. So definitely has to do with people.
Joseph Fung: What a life-full answer. Kenny, thank you so much for such a great conversation. This has been a blast.
Kenny Goldman: Thank you, Joseph. I’ve loved it as well always having a great conversation with you and love what you and the team are doing at Uvaro, so, I appreciate your support to the you know Toronto sales community and what you’ve got going on here.
Joseph Fung: Well, thank you I’m looking forward to getting a chance to continue this conversation in person once the events are again back in person. But in the meantime I hope you’re enjoying the summer weather. Staying safe. And hoping you’re having a great time.
Kenny Goldman: Definitely. I’m trying to, yes, as much as i can soak up the sun.
Joseph Fung: Great stuff. We’ll chat soon, Kenny.
Kenny Goldman: Take care. Thanks, Joseph.