hello there! this is my first time posting/a new member of bravado. a little color to go with my question... I started my career in the VC world 6 years ago as an analyst then associate for deal vetting & due diligence.
One of the portcos of the VC is an AI SaaS company, we'll call it Ligma, that (at the time) was primarily FinTech focused with some neat IP. Fast forward to 2018, the founder of the VC asked me to do a deep dive into the AI services & consulting space for a potential newco leveraging Ligma's IP (services vs products kept the 2 entities from competing with each other... in theory). At the time, there weren't many great SMB-sized AI consulting shops in the market so the VC and Ligma decided to pull the trigger and form an AI consulting company that would be majority owned by Ligma. They got a stellar IBM exec to be CEO and needed a #2 person, I got the blessing from the VC's founder to join this new company, which we'll call Bolt and started my start-up career. At the time I had the title of project manger, was given a meh salary ($70k) and some equity (15 bps) and was the second hire of the company. Fast forward a year to March 2020 and Bolt had 0 sales, the CEO was a disaster and resigned. This left me, myself, and I with 4 off-shore developers and about 10 months of runway (burn was really low). Our board decided to give me a shot (they really didn't have any other choice) and made me President & COO while the CEO of Ligma (also board chairman) advised me daily and functioned as a guiding voice rather than a full-time CEO.
Tough af to become the face of a company during the legit start of the pandemic, with no product, no product market fit, no pipeline, nada. I decided to bring the company in a different direction and went to the strengths of our developers... web scraping. We combined web scraping with NLP technology licensed from Ligma to do some really cool stuff. By December 2020, I (by myself) brought in $250k of sales through a lot of hustling and bullshitting to make us look bigger (including keeping my title on LinkedIn a more junior sales role). I hired a hell of a marketing person to start inbound lead gen (small team, didn't have time to do prospecting myself on top of running the company, closing deals, doing project management with the developers, etc.). By March 2021, 1 year after I took over, we had ~$1.25M of booked ARR (mainly a chunky, $900k 3 year subscription deal). I hired a product manager, staffed up on the product side, and things were looking bright for this little company I had built. Then the CEO of Ligma called me saying they wanted to acquire Bolt because they needed a rockstar selling machine for their commercial sales (which was non-existent) and basically wanted our book of business to jumpstart it. We had a board meeting, I discussed my apprehension to the idea as well as the positives and ultimately the board was very gracious and made sure my apprehensions were addressed in the deal docs (namely, every member of my team needed guaranteed equal or higher job positions at Ligma). That acquisition was done in July 2021 (never thought I'd go through an acquisition at 27 years old but there I was). Side note, hardest part about acquisitions is people management.
I started out at Ligma under a pretty seasoned CRO, built a name brand AI company from $1M to over $100M so lots to learn from him. Only problem is, Ligma's product and strategy was in shambles. The tech is solid and valuable af, but Ligma didn't know how to operationalize/monetize it. The CRO saw this and went running for the hills roughly 5 months into starting. This left myself (again) with no product to sell but this time I had 2 SDRs, 1 sales ops manager, and 1 SDR manager at my disposal. And oh by the way, the CEO of Ligma is in the mindset that it's his way or the highway. Ligma had always done services business, making custom 1 off solutions for customers and now he wanted Ligma to be a product ARR business. Massive shift both from a sales and operations perspective.
Flash forward to today. I now have 2 ISRs, 2 BDRs, 1 sales ops/bdr manager (same person doing both) and maybe $500k of sales total with 0 working products to sell... meanwhile the gov't side of the business is getting all the resources/love while commercial gets a bag of peanuts and a "show me the sales, you'll get more resources." Got the message last week that the company wanted to reassign me to product because 'things weren't working out', to which I say buh-bye. The company is in shambles operationally, fiscally, etc.
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So my question... with someone with 5 years' experience selling AI SaaS/services to SMBs up to Fortune 100 companies, with deal cycles that range from 2 weeks to 10 months, deal sizes from $5k to $1M+ ARR, titles that include President & COO/Director of Growth/Director of Sales, how do I market myself effectively in the job market where my previous titles may not tell the whole story?
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