The situation
I joined Smartsheet in 2014 as VP of Digital Marketing. ARR was $18M, and the company grew the way the best bottoms-up products do: someone started a free trial, invited collaborators, and the thing spread sideways through an organization without anyone in IT ever approving it. Nobody called that product-led growth yet — the term would not be coined for another two years.
It worked, and it had a ceiling. Self-discovery brings you users. It does not bring you a six-figure contract.
The idea
Instrument the self-serve motion well enough that it tells you where the enterprise deals already are.
Every trial, every collaborator invite, every team that outgrew its plan was a demand signal. Read those properly and we would not have to guess which accounts deserved a salesperson — the product would tell us. Sales would not be bolted on top of the funnel. It would be aimed by it.
What it took
- A demand engine. Marketing automation, analytics, and experimentation-driven acquisition, stood up as a global function that did not previously exist. ARR grew from $18M to $64M over that stretch, and I kept demand generation for the rest of my decade at the company — through commercial sales, and through the CMO years after.
- Scoring the signal. By the time of the S-1, Smartsheet was generating over 100,000 new trials a month, and inside sales worked an internally built lead-scoring engine that picked out the trial users and collaborators most likely to convert. Field sales was pointed at accounts that already had a deployment and a visible expansion opportunity.
- Refusing to split the org. In 2016 I took commercial sales alongside demand generation — 400+ people across sales, SDRs, and inbound and outbound marketing under one roof. That was deliberate. The handoff between marketing and sales is where product-led companies leak, and there is no handoff if there is no seam.
- Adding a motion, not replacing one. Self-serve and inside sales kept doing what they were good at. The sales-led motion went on top, aimed only where the product had already proven demand.
The outcome
- Commercial ARR grew from $64M to $550M, through the 2018 NYSE IPO and roughly 40%+ annual growth in the years after it.
- The move upmarket showed up in the public numbers. Customers worth $100K+ in annual contract value grew 120% year over year in Q3 FY2020 and 138% by year end; $50K+ customers more than doubled. Dollar-based net retention ran 130–134%, and higher still among larger accounts.
What I would tell another CMO
Product-led and sales-led is a false choice, and treating it as one costs you the upmarket. The product is already telling you which accounts are worth a salesperson.