From Yogurt Shops to Unicorns: Jessica Gilmartin’s Unlikely On-Ramp to Tech

Before she carried dual CMO + CRO titles at Calendly and led revenue marketing at Asana, Jessica Gilmartin was slinging frozen yogurt in the Bay Area. In her recent interview in The GMTnow Podcast with Scott Barker, her franchise thrived—and so did her appetite for building from scratch. That retail tour “cemented a true ownership mentality” that she now expects from every team member: “My job is to make the company successful … When I see there’s a challenge, I just jump into it.”

The through-line for wantrepreneurs: your first venture doesn’t have to be glamorous, but it should hard-wire bias for action.

When Product-Led Growth Hits the Enterprise Ceiling

Both Asana and Calendly exploded on the back of bottom-up adoption—individual users got value on Day 1 and eagerly shared the product across their orgs. Eventually, usage requests sounded less like “Can I add one more teammate?” and more like “We need SOC2, SCIM, and a global license.”

That customer pull, not an internal mandate, signaled it was time to layer a sales-led motion. As Gilmartin notes, once ten or a hundred users are onboard, the product itself creates exponential value—and enterprise expectations .

Key friction points in the hybrid PLG/SLG world: competing calls-to-action on the website, dueling resource requests from growth and enterprise PMs, and staffing two distinct marketing muscles under one roof. “It’s like running two companies,” she admits .

Founder takeaway

Let the product and paying customers dictate when you graduate to SLG—and be prepared for brutal prioritization debates once you do.

Data: The Unsexy Growth Accelerator

Gilmartin is blunt: “Data is the most excruciating thing and it’s the least sexy thing, but it’s the most important thing.”

At Calendly, PLG and SLG lived in separate tech stacks—Iterable, Chargebee, and product logs on one side; Salesforce and RevOps tags on the other. Analysts routinely pulled bad reports because field definitions differed by team. The fix was organizational, not technical: an operating committee of cross-functional directors met weekly, while a C-suite governing committee unblocked resourcing every two weeks .

Founder takeaway

Invest in a unified data dictionary early. Without it, your fanciest attribution model is just expensive fiction.

Practicing “Creative Destruction” Inside Your Marketing Org

Gilmartin asks her marketers to reassess—and often replace—most campaigns every quarter. “If everything works, it means you are absolutely not trying hard enough.”

That experimentation ethos is balanced by clear annual north-stars so the team avoids chaos. Strategy (e.g., “move up-market”) stays fixed; tactics are disposable. Webinars may shrink from 60 minutes to five, or ad dollars may pivot from Google to micro-influencers overnight.

Founder takeaway

Set immovable objectives, then give teams psychological safety—and budget—to burn the playbook every 90 days.

Blurring the Lines Between Marketing, Sales & Success

Gilmartin rejects the tidy funnel cliché: “Everybody is responsible for the customer … worrying about attribution is very, very silly.”

Her rule of thumb:

• Marketing obsesses over paying customers—“That’s your ICP; if no one will pay, you have no ICP.”
• Sales contributes to upsell motions born in product telemetry (think integration-triggered PQLs).
• Customer success feeds usage stories back into product and marketing.

When everyone co-authors the plan, misses aren’t blamed on one function; they’re shared learning debt .

Playbook for Early-Stage Founders

1. Validate PMF before hiring marketing. “You can’t market your way into product-market fit.”
2. Follow the money. Segment by industry, company size, and stack to find customers with highest LTV and NRR, not the loudest free users.
3. Instrument product signals. Integrations, team seat thresholds, or security feature clicks often predict readiness for a sales conversation .
4. Form ad-hoc “SWAT” committees for hairy, cross-functional problems. It drives urgency and accountability, fast.
5. Default to radical transparency. Celebrate flops publicly to normalize risk-taking and accelerate iteration.