Revenue architecture · Seed through Series C
You've found the product. Now find the growth engine.
We design the systems behind durable revenue — sales motion, retention infrastructure, and expansion architecture — for startups in fintech, digital assets, AI, and developer platforms.
Work with us →Turn ambiguity into predictable growth.
What we build
Three disciplines. One revenue flywheel.
Sales architecture
Pipeline design, ICP definition, and repeatable motion — built to survive the transition from founder-led to team-led selling.
Retention infrastructure
Onboarding systems, health scoring, and CS frameworks that reduce churn before it compounds into a structural problem.
Expansion frameworks
Upsell trigger identification, land-and-expand strategy, and NRR optimization — turning your existing base into your best growth channel.
Selected outcomes
Operator credentials, not advisory theory.
Revenue engine
$2M → $15M ARR
Served as GM across a scaling blockchain infrastructure company — designed and ran the full revenue operation across sales, CS, and account management.
New business line
$0 → $2M
Founded and built a net-new business line from scratch — ICP definition, GTM motion, and partnership model. Zero to run rate as operator, not advisor.
Lifecycle optimization
115% NRR
Implemented QBR processes, expansion targets, health scoring, and account frameworks driving above-benchmark retention.
Most revenue problems aren't sales problems.
They're architecture problems.
How we work
Diagnose
A revenue system audit across pipeline, retention, and expansion. We find where the model is breaking — and why it's breaking there.
Design
Build the architecture — ICP definition, lifecycle frameworks, and revenue motion — tailored specifically to your stage and market.
Install
Implement the system with your team. Establish operating cadence, accountability structure, and the playbooks your people will actually use.
Scale
Refine the model as the company grows and complexity increases. The system evolves with you.
Where we focus
Financial technology
Payments, lending, infrastructure — where compliance complexity meets GTM urgency.
Blockchain infrastructure
Institutional adoption, enterprise sales, and the revenue motions that work in a market traditional playbooks weren't built for.
Applied AI
Selling technical products to non-technical buyers in markets that didn't exist two years ago.
Developer platforms
Bottom-up growth with top-down conversion — where PLG meets enterprise.
Who we help
We build the system to get you to the next stage.
Founder-led sales
Closed on personality, not process
Repeatable team motion
A playbook the whole team can run
Early traction
Wins, but no pattern behind them
Structured pipeline
ICP defined, motion standardized
First customers
No system to keep or grow them
Expansion engine
Lifecycle model driving NRR above 100%
Inconsistent growth
Revenue that's hard to forecast
Predictable revenue
A system leadership can plan around
About
Pleasant Street Advisory is led by Avi Meyers, a revenue and GTM operator with 16+ years across fintech, digital assets, and SaaS.
Avi has designed and run revenue organizations scaling from $2M to $15M ARR, launched new business lines from $0 to $2M, and built forward-deployed customer models that drove 115%+ net revenue retention — including at a leading blockchain infrastructure company navigating institutional adoption.
The firm exists to bring operator-level experience to startups navigating the hardest phase of growth: when the product works, but the revenue system doesn't.
In 30 minutes we can usually identify the biggest gap in your revenue system.
Schedule a discovery call →