My Journey at Thinkific - Launching a Sales Team and New Business line at a Product Led Growth Company

Launching a Sales Team and New Business line at a Product Led Growth Company

Well, last Monday was unexpectedly my last day as VP Sales for Thinkific.?

3 years and 9 months later, I find myself sitting with a coffee, feeling a whirlwind of emotions but above all else, a feeling of deep gratitude for what has truly been, the wildest of rides. I was told recently that I don’t do a good enough job of celebrating and shining a light on my team, and my personal achievements, so I wanted to put together a quick post to share a bit about my story at Thinkific. While I am sad it has come to an end, when I think back to sitting down with Greg Smith 4 years ago for a casual chat and a burger, I don’t think I could even have dreamt up the exciting, inspiring, educational journey I was about to go on, and more importantly the lifelong friendships I’ve been fortunate to build along the way.

I joined Thinkific as their first VP of Sales, in fact I think I walked in the door as their first ‘VP’ of anything - so no pressure at all. In one of our first Senior Leadership Meetings, Andrea Merson (One of the best marketing leaders I’ve ever had the privilege to work alongside), put up her hand and said, "Greg, I’m a bit confused about why Adam is here? I thought Sales was going to be ran separately from the rest of Thinkific?" Not exactly what you want to hear on your first few days on the job, but definitely helped me understand the nature of the challenge ahead.

For those reading who don’t know Thinkific, it’s an SaaS online learning platform focused on driving revenue from digital education, and before I joined had operated as a freemium driven, Product-Led Growth company. At that stage a ‘Sales Team’ was simply not a thing, mind-blowing for me as my background was working for companies where Sales was responsible for 100% new revenue, I’d now joined one where Sales was responsible for 0%. It's been pretty cool to watch along the rise of the concept of 'Product Led Revenue' over the past few years and my hope is that our journey at Thinkific can help new Sales and GTM Leaders looking to succeed in similar positions. (check out Correlated and ?? Breezy Beaumont and Kyle Poyar for more great content on this topic)

The first thing I did seems pretty obvious to most Sales Leaders - but at that stage Thinkific wasn’t doing too much of - talk to the customers coming through our door. It became apparent very quickly that Thinkific wasn’t just attracting the Solopreneur, Digital Creator persona that the platform was originally built for, but that there were companies of all shapes and sizes coming through our doors every day. A Sales Leader I was fortunate to work with before Thinkific (Ian Gilbert) always emphasized to me ‘No pain, no deal’, so my first step was to find out why? What problems are these customers looking to solve? And why, in a world of many, many Learning Management Systems (LMS), were so many customers finding their way to Thinkific, clearly they had a problem to solve.

I’m a firm believer as a Sales Leader that you have to understand how to sell a product yourself before you can ask others to do it, never mind train them and coach them. So I did something I hadn’t for a while, hit the phones. I remember one of our first calls with Brett Fox? over at Photzy, (With Sara Doole helping me paper over the cracks of my very limited product knowledge) and having my mind blown at the scale his small, 5 person business was operating at. He was looking to market and sell his photography courses to hundreds of thousands of people and businesses, a number that is now in the millions. The next day I was speaking to a VP at a large telecommunications company looking to educate their customers on a global scale. At this stage it also became apparent that there wasn’t just one or two of these types of businesses engaging with Thinkific each week, but hundreds every week. There was a clear need to build a team, I was lucky to start with an absolute gem of a person in Pauly Dymel who came over from our CS team as an AE, and very quickly after that bring in Brian Kingston straight off the boat from Ireland as a second AE.

?? The 'OG' Sales Team, July 2019

Back then we were selling Thinkific ‘Enterprise', a name that didn’t really reflect what we were selling, and our marketing at Thinkific was largely focused on very early stage Digital creators. As I listened to more and more customer calls I had the realization that for Thinkific to really scale a successful Sales team, we needed something to sell that the team could believe in, and that we should repackage our offering, and more importantly reposition the platform to accommodate the significant inbound demand we were seeing. Most importantly, we had to work out WHY customers were succeeding on Thinkific, WHY we were better than the litany of Enterprise LMS platforms on the market, and then make those key differentiators clear to prospects. (April Dunford you might not remember the 45 minute convo we had back in 2019 - but your positioning advice led to a now $10m business line 3 years later). Above all else, we needed to make Thinkific’s differentiated value simple to understand, and make the platform very easy to buy.

It was at this stage, around April 2019 that we made the decision to launch ‘Thinkific Plus’, a new Thinkific plan type built for high scale and mid-sized businesses. Looking back at the slides I presented to Greg, Miranda Lievers and the rest of the team back then, as much as my design skills left a lot to be desired (and still do), the value proposition was clear, and is still very relevant today. Scalability, Reliability and Flexibility. It’s been interesting to watch more and more PLG companies stretch upmarket over the past ten years, and the message is clear:

People want to use well built software designed for the user, not enterprise software built for a feature list ripped off some janky RFP. People want to buy in a simple, customer focussed way.?

And users are just that - people. The success of PLG shows that the approach of building for B2C vs B2B is outdated and nonsensical. It seems pretty clear to me that software needs to be built for the people using it, and that the traditional B2B selling approach has also gone through a much needed transformation back to focusing on the experience of the buyer.?

As much as I might like to offer up ideas (probably way too many if you ask the Thinkific Plus marketing team) around product marketing and demand generation marketing, it’s definitely not my forte, so we brought in our very first dedicated Plus marketer, Amber Muench. WHAT.A.HIRE. I’d been lucky enough to work with Amber back at Rise Previously, so I knew she was an incredibly adept person, but when I look back at her achievements with Thinkific Plus I am truly in awe. I know T-shaped marketer is a popular term for an all faceted marketing leader, but in Amber’s case it would need to be more of an octagon shape ;). Amber helped create the positioning, website, pricing iterations, collateral, countless campaigns, competitive intelligence and so many other areas. Amber reported to our Director of Product Marketing Gary Allen , who is not only an insanely smart Product Marketing leader, (and makes a mean cocktail) but also somebody I could bounce ideas off of and know that I’d get a direct, honest opinion back. (even though I’d argue it at the time of course). During my time at Thinkific I learnt a ton about product marketing, pricing strategy and positioning from people like Gary, Amber and Michael Vasilev later, and I think to be successful in SaaS Sales it’s critical for any Sales Leader to have a close working relationship with the Product Marketing leadership and team. The insights collected on Sales calls like Gong can be utilized across Product Marketing and Product Management, and the positioning statements and customer research those groups are working on are a goldmine for value proposition creation and competitive positioning narratives for the Sales Team.

The insights collected on Sales calls like Gong can be utilized across Product Marketing and Product Management, and the positioning statements and customer research those groups are working on are a goldmine for value proposition creation and competitive positioning narratives for the Sales Team.

So, Plus was launched in August 2018 (https://www.thinkific.com/blog/introducing-thinkific-plus/). We were also starting to see some real traction in the Sales team, with our first $500k ARR quarter. We bolstered the ranks and specialized, splitting the team into SMB and Mid-Market AEs, with SMB working a hybrid AE/BDR role of helping self-serve customers choose Thinkific, and also identifying and passing over Thinkific Plus leads for the Mid-Market team to close. The debate of ‘Well wouldn’t those self-serve customers close anyway?’ was never truly answered, despite our incredible head of data at the time Steph Carew's best efforts. We also added two more rockstars to the team in 2019, with Christina Lupieri (Thinkific’s most successful AE ever and now impressive Sales Manager) and Hunter Murphy, an SMB AE then, now a leading Mid-Market AE and still closing great Plus deals. In addition, Thinkific brought on a new Chief Revenue Officer in Craig Ryomoto, another person I would learn an insane amount from, and somebody I now consider to be a great friend.

The Sales leads were coming from a variety of sources, some from the traditional B2B marketing model, driven by paid ads and content marketing, and we were seeing the Product Led Growth flywheel turn, with successful self-serve customers referred by our award-winning Customer Support Team (led brilliantly by Veronica Howes and Yinyi Tan ) upgrading to Thinkific Plus, and hundreds of businesses testing Thinkific out on our free plan. We also?put in place a fairly simple lead scoring mechanism based on demographic customer data, to try and recognize the best fit businesses engaging with Thinkific. It was an exciting time to be a part of the Sales Team at Thinkific, definitely ‘building the boat as we were sailing it’, but the early results were encouraging to say the least.

What happened next, nobody at Thinkific was prepared for, in fact nobody anywhere. When the pandemic hit in 2020, it negatively impacted many industries - the online learning space however, was not one of those industries. In fact it was the exact opposite. At Thinkific we saw demand explode, across all businesses from digital creators to brick and mortar stores. It was a whirlwind of a year. We added new customers at an unprecedented rate across all plans. Our Account Executives were taking 10-12 calls a day, and our self-serve business reached customer acquisition levels from March to June that I’m not certain will ever be matched. The best part? Thinkific was positioned perfectly to truly help people in a time of need, and allow people all over the world to use the pandemic as an opportunity to create when previously they hadn’t had the bandwidth or inclination.? I’ll always be super proud of the way the company showed up that year, particularly the Sales Team - which was now growing significantly. We added a new SMB Manager, (Dominic Jan Sunga Sungha), and new Account Executives (Gareth Short, Damien Woodfull, Meggi Mah, Jimmy Ly, Ian Kobylanski),? Alongside this growth in Sales, our Plus Marketing team increased in size and our CS team as well. Plus finished 2020 at around $3.7m in ARR and growing fast with an amazing cross functional team. Mind-blowing to see how far our idea was growing into fully fledged startup within Thinkific.

As if what transpired in?2020 wasn’t quite eventful enough, Thinkific took advantage of favorable market conditions and released its’ Initial Public Offering on the TSX in April of 2021! #THNC was a massive win for everybody at the company, and an incredibly validating and educational experience. Also beyond impressive in terms of the speed that our finance team was able to complete what is a huge undertaking in record time, with immense support from Julian (Jay) Rhind , Fraser H. and the entire Rhino Ventures team, who've been unreal to work with over the years. There was so much hype around Thinkific globally, and I was personally thrilled to be a part of my second exit in as many companies. While the covid tailwind for the online learning space had relaxed a little, Thinkific Plus continued to grow at a phenomenal rate of 100% YoY, finishing the year at $7.4M In ARR.

We continued to invest in Thinkific Plus and grow the Plus team to over 50 Thinkers across multiple departments. The most satisfying part for me was seeing the Sales team flourish, and seeing the Sales culture we’d built around guiding principles like ‘More than just a number’, ‘Different Together’ and ‘Succeed as a team, Fail as a team’ yield fantastic results. My advice to any Sales Leader building a team, is to create those principles early in the journey. Ask yourself, 'What kind of team do we want to be?' and also, possibly more importantly, 'What kind of team do we not want to turn into? The answers to those questions helped us to shape a Sales culture that was different to the norm, and was centred around continuously leveling up the team itself, with our customers a close second, and revenue as the output but not the only focus. 'Team, Customer, Revenue' was our three word mantra, although I should add that we generated a lot of the latter as a result of that approach. We added phenomenal, like minded Sales Leaders like Jon Clement-Smith , Marianna Adamian and Brett Gillespie and continued to promote from within, as well as bringing great people in from the outside, like our Director of Plus Marketing Christie Horsman. When I started at Thinkific I wanted to build a different type of Sales Team, that was results driven but focused on the inputs not just the outputs. We built a diverse team who brought so many different backgrounds, genders, races and above all personalities, and there’s no doubt in my mind it was the diversity of our team that was a key driver behind our success.

Equal Opportunities in Action ??

It was truly a special time to be at Thinkific, and I’m so proud of the team we built and our accomplishments. Thinkific finished the year of 2021 with over 400 people, thanks to an amazing CORE (Culture, Operations, Recruitment, Education), led by Tia Fomenoff , and supported by, Amanda Nagy , Ryan Anderson , Mira Lehan, CPHR, CLC , Amanda Turcotte and many others. I think the challenge with growth at that scale is maintaining the great things about the culture, while leveling up operationally access the entire business. I think we did a great job at the former, using the Top Grading methodology for hiring to ensure we brought the right people, but in retrospect didn’t invest heavily enough on the operational side, something that the team is currently focused on fixing to allow for the next stage of Thinkific's growth.

2022 has been more turbulent, and brought with it an economic downturn, as well as a workforce reduction that hit everybody hard. We lost some of our Sales and Plus team members as a result, there’s no easy way to say it, layoffs suck. With all that was happening I’m so proud that our remaining team members rallied, and actually achieved our two highest ever quarters in terms of Plus MRR added, with somewhat of a skeleton team and limited resources. It really is a testament to a truly amazing team what we’ve been able to achieve. Despite my time ending last week, I feel truly grateful to have played a part in it. Building a new business line is hard. Setting up a new Sales Team at a PLG company is hard. And growing the Plus business line to a healthy $10 Million in Annual Recurring Revenue over a three year period is something I will always look back on with great pride.

Photo Credit to Emily Weiss - another of the absolute best! ??

Leaving Thinkific last week I was able to look back at the past few years and reflect on one of the best times of my life. Since December 2018 when I started with the company it has grown from $6.5Million in ARR to $50 Million, from 60 people to 400, and of course went public. And while these achievements are significant, I’m pretty sure when I find my dusty Thinkific hoodie in a box in 30 years, it won't be the numbers I remember, it'll be the people. The amazing relationships I built. The customers we helped. And SO much fun!

Thank you to everybody I’ve mentioned in this post, and to everybody I haven’t. (There are MANY). For those still at Thinkific, I wish you my very best. And to whoever is fortunate to work with the Sales and Plus teams next, I wish the very best in terms of luck and success. You’ll be a part of something truly special, and? I'll be cheering you all? on from the sidelines. ????

A few additional content pieces helping to tell a bit more of the story:

https://podtail.com/da/podcast/saas-open-mic-by-chartmogul/building-sales-at-a-product-led-company-with-think/

https://medium.com/thinkific/a-day-in-the-life-of-an-account-executive-at-thinkific-895808a76b62

https://medium.com/thinkific/thinkifics-sales-team-transforming-sales-culture-769c54ec857f?

https://www.blueboard.com/blog/tips-to-improve-sales-culture / https://www.blueboard.com/blog/tips-to-improve-sales-culture-part-2?