Andrew Brinkman

Head of Product at Leap · Aurora, Colorado · fifteen years across vertical SaaS, streaming, and sports tech

I ran a retention turnaround at a $200M ARR company. At Leap I run product with six squads and fill whatever the team is missing myself.At Buildertrend I ran twelve squads inside a 115-person product and engineering org and took annualized logo retention from about 60% to 85%. Since March I have written the strategy, run fourteen customer interviews, hired four senior people, taken ownership of pricing and packaging for the AI-native rebuild, and built the tools and prototypes the work needed when no one else had the capacity.

Leap Buildertrend Bonusly Sling TV Hudl
$25M+ARR, Hudl Assist, built from zero
~60% → 85%Buildertrend annualized logo retention over the tenure66% to 73% in the target segment in year one
12% → 4%Buildertrend churn inside 90 days, target segment
<5% → ~15%Bonusly enterprise ARR mix
4 quartersSling TV subscriber growthfirst since 2018
177 changesShipped to Leap customers in July and Augustsix squads, four products

Work

Leap
Gated
Crew packaging: the structure I proposed, and the one that shipped
I wrote the value-metric analysis and a graduated per-seat structure with a pooled AI allowance. The pricing alignment chose a flat fee with unlimited users and per-job charges instead. The log says why it won and what I took from it.
Open case study Flat fee plus per-job, shipped
Built soloGated
Product Signals: a churn-attribution engine
Places every churn dollar in one of five evidence-based states and ranks what to build by retention dollars. Reported that product drives only a minority of churn.
Open case study Product drives 10 to 16% of churn
Gated
Lily: an AI receptionist for the calls contractors miss
Spec, business case, and code: a four-hour proof of concept, a hardened MVP, and now a rebuild into Leap Crew as a hired AI crew member.
Open case study In rebuild, not yet live
Gated
Account health: the at-risk signal customer success runs on
A fairer health score with an activation gate, an activation score written into Salesforce onboarding cases, alerts with the owner's name on them, a backtested early-churn detector, and a value ladder for Crew. A hundred merged pull requests.
Open case study 100 PRs, 1 workbook retired
Gated
Fourteen switch interviews, and the Crew roadmap they produced
Ran the jobs-to-be-done program myself, built the skills and pipeline that structure and synthesize every transcript, and turned the findings into Crew's defining commitments and its ICP roadmap.
Open case study 14 interviews, 3 Crew commitments
Turnarounds
Gated
Buildertrend: fixing failure-to-launch
Replaced open-ended onboarding with a gated, opinionated setup path, timed with the company's move to annual contracts. Target-segment logo retention rose seven points in year one and annualized logo retention went from about 60% to 85% over the tenure.
Open case study Logo retention ~60% → 85%
Bonusly: cutting a product to build an enterprise motion
Killed a survey product diluting the platform, repackaged around an enterprise tier priced on outcomes with the analytics, SSO, and integrations enterprises pay for, and shipped a white-label deployment for Disney as a platform capability.
2022 to 2023Enterprise mix <5% → ~15%
Sling TV: four quarters of growth, and a feature retired
Product strategy behind four consecutive quarters of subscriber growth, Sling's first since 2018. Sunset Watch Party after the data showed users gaming it for free access, despite prior commitments to expand it.
2021 to 20224 quarters of growth
Zero to one
Gated
Inside Leap Crew: eighty pull requests from the head of product
Thirty-two CRM features in June when the squad was short on hands, a measured cut to what the AI assistant costs to run, a path from the assistant to a human, and an automation that keeps the user guide true on every merge.
Open case study 80 PRs, AI cost cut
Gated
Hudl: took it beyond football, then built a business on top
Built the basketball platform from the ground up (8% to 60% high-school share in two years), then Assist, a video breakdown service, into a $25M+ ARR line.
Open case study $25M+ ARR built

Screens

Product Signals, churn dashboard
Churn, by controllability
Trailing twelve months · ties to Salesforce weekly · refreshed Monday
10–16%of churn dollars product-driven
5evidence-based states
~4xearly cancellations caught vs old rulebacktested
Every churn dollar, one state tie-out green
Unpreventablecompany gone, corroborated
Verified preventable, productwhat product can build
Verified preventable, servicerouted to customer success
Verified not preventableright-sized, still billing
Undiagnosed bandworked down weekly
Lily, after-hours call
Incoming callafter hours
Receptionist answered"Thanks for calling. You've reached our automated receptionist."
Caller identified from the calling numberdone
Lead created in the CRMdone
Inspection booked, Thursdaydone
Emergency? Warm transfer to on-callrule
Callback task assignedFrom Receptionist · reason logged
Crew packaging, the structure
Your plan this month (the proposal)
Proposed: graduated per-seat rate · pooled AI credits · attach lines outside the meter
AI allowance, pooled across the account within allowance
Each seat prices at its own band's rate, cumulative, never retroactiveno cliffs
Overage above the pool, with caps, alerts, and a dashboard at launchmetered
Receptionist minutes and fintech billed as their own attach linesoutside the meter
Early-churn alert
#onboardingtoday
New Account Low Usage day 45
Fewer than 3 jobs in the last 30 days
First paid seat45 days ago
Onboarding casenot required
AlertedOS
Why this ruleBacktested on a year of new deals. Catches about four times the early cancellations of the rule it replaced.
Product ops, every morning
Morning reports
Jira and GitHub in, written updates out
New report
Daily 2
Roadmap site rebuilt from Jira
06:00every morning
Crew update from production deploys
Claude-writtento the CEO
Weekly 2
Hygiene digest, one per PM
Fridaysstale tickets, missing fields
Leadership report
Claude-writtenfrom real tickets
Always on 1
Bug-triage agent
watchingpriority lanes
draft fixes only behind safety gates

Leap

Head of Product since March, reporting to the CEO. Contractor software with two legacy products, a retention problem, and a bet on an AI-native rebuild.

The mandate, and how it changed

  • Hired to fix retention in the legacy products. I wrote the 2026 strategy around holding the customers we have, ran fourteen switch interviews myself, built the churn evidence the roadmap is argued from, and rebuilt the account-health instrumentation customer success and onboarding use to decide who to call.
  • Then the company went all-in on Leap Crew. In late August the AI-native rebuild became the future of the business. I am reorienting the team around it while still holding the retention goals: six squads with one mandate each, four senior hires in four months, and a plan that moves capacity to Crew without a second reorg.
  • Six squads that run without me. One mandate per squad, one PM per product with the outcome, and a new Enterprise team behind the third strategic intent. I teach thin slicing and I review; when the Crew PM pushed back on the packaging, two alternatives were built to the same depth and scored against mine. I am hands-on only where the work has no other owner.
  • Make Crew a business. I own how it is packaged and sold.
  • Where it stands. The squads shipped 177 customer-facing changes across 61 epics and four products in July and August. Crew reached its first paying customers in September. The legacy products are on track to hit the year's retention target.

How the squads run

  • An Enterprise team with a boundary. Enterprise requests had no stable owner, so they arrived as interrupt-driven custom work for whoever was loudest. I stood up a dedicated team under a senior PM with its own engineers, with a rule the team can hold without me: custom integrations go through product prioritization, one-offs are a no unless they have a one-to-many case, and intake starts with a conversation rather than a ticket. Within six weeks the team was running its own portfolio dashboard and cadence.
  • PMs own their roadmaps. The Integrations PM has full autonomy over the integrations roadmap, with a directional check from me, and is sequencing Crew integrations against revenue, usage, and churn signals. The Integrations and Data and Reporting squads decide for themselves how to wind down their CRM work while standing up Crew roadmaps. Product Council is an inform-and-veto forum; the product team sets priorities.
  • Standards instead of ceremonies. An initiative is real when it breaks into shippable slices with dates that reflect confidence. "Done" means the quality bar is met, and we distinguish the internal deploy date from the customer release date, committing to customers only when confidence is high. No story points were imposed; squads use them if they help.
  • Evidence as the price of autonomy. Every product leader keeps a small group of customers they can call and spends time in the field. The designer's growth goal is two or three customer conversations a week and a seat in early problem framing. When a PM's direction looked wrong, the ask was to come back with evidence from three customers that changed it.
  • Hire for judgment. The PM interview bar tests continuous discovery, thin slicing, and real AI product judgment. Four senior hires in four months, each with a written brief, and a PM backfill so the enterprise lead was not doing two jobs.

Shipped against the top churn reasons

The left column is the churn ledger's ranking of why legacy customers leave. The right column is what the squads shipped against it between March and September.

Onboarding stalls before first valueFirst-run templates and configurations for new subscribers; a migration utility that imports from the main competitor's CRMJuly
Proposals and contracts painful to build in-appThe rebuilt document editor through beta, mobile, and post-launch improvementsJuly to September
Financial reporting too shallow to run the books onOne definition of job profit across the CRM and the reporting tool; a QuickBooks health center and sync fixesAugust to September
Price-guide and template setup, on the sales appCategory cloning and onboarding efficiencies that cut price-guide setup workJuly
Field photo capture and upload reliabilityPhoto experience rebuilt end to endAugust
Texting scattered across threadsText and notification fundamentals; consistent automation triggers across workflow stagesJuly
Consumer financing limited to a single lenderLender expansion and consumer financing in both legacy productsJuly to August

How I lead

What I hold the team to

  • Closest to customers in the vertical. Regular, non-reactive conversations. Product is not support.
  • Every initiative has a through-line to retention, grounded in conversations and usage data.
  • Move one or two needles at a time.
  • Thin slices, continuously, and finish. No big-bang launches; open quality issues mean we are not done.
  • Extreme ownership. We do not let the world happen to us.

What the team gets from me

  • Clarity on priorities and what good looks like, so nobody is guessing.
  • Context as well as direction: the customer, business, and strategic reasons behind where we invest.
  • Air cover from noise and work that adds nothing.
  • Timely decisions and direct feedback. No drive-by criticism; you know where you stand.
  • No micromanagement. I do not hire capable people and then tell them how to do the job.

What people I've worked with say

All recommendations on LinkedIn

"A direct communicator, Brink lives the 'strong opinions, held lightly' mantra and is an evidence-based decision-maker. As a manager, I found his insights invaluable as he helped me develop as a product manager. He challenged me in the right ways and helped me see around corners."

FE
Ford EnglanderReported to Andrew at Hudl · now Staff Product Operations Manager, Confluent

"He had complete trust in handing over full operations of a squad to me, and his hands-off management was much appreciated. Andrew cares deeply about the craftsmanship of product management, and his views there have helped create one of the healthiest product organisations I've worked at in my career."

AJ
Ayman JawharReported to Andrew at Hudl · now a builder CTO and former CPO

"Andrew is able to formulate clear product vision, in both a realistic near term and innovation for the future. He makes it easy to work as a designer within a product org because he respects the design process and lets designers work alongside product in a collaborative effort."

MD
Matt DeanWorked with Andrew at Sling TV · Senior Product Designer, Sling, Roku, DocuSign

About

At Hudl I learned to pitch and build: Assist went from an idea at a company call for ideas to a $25M+ line. At Buildertrend I learned to change an organization that did not want to change: twelve squads, a sales motion retrained, logo retention up 25 points. Between Hudl and Buildertrend, Sling TV taught me in a year that a billion-dollar consumer platform was not where I do my best work, and Bonusly taught me to cut: a survey product killed, an enterprise motion built, and a layoff that took most of the product org with it. At Leap, as Head of Product, I build the evidence first and let it argue: fourteen interviews, a churn ledger tied to finance, an audit of my own AI that came back half wrong, and a finding that product causes a minority of churn, reported before anything else. At every company I have retired something people were attached to: Watch Party at Sling, a survey product at Bonusly, a churn signal at Leap that flattered my own lane.

My employers have ranged from growth-equity backed (Leap, backed by Nexa Equity) to PE-backed (Buildertrend, backed by Bain Capital, HGGC, and Serent Capital) to venture-backed (Bonusly, which closed its Series B led by Ankona Capital while I was there; Hudl, backed by Bain Capital) to a public company's streaming arm (Sling TV). I hold an MBA from the University of Nebraska–Lincoln's Raikes School and started as a software engineer at IBM. I coach product talent; several people I developed now run their own product organizations.

Get in touch

Email is best. The gated case studies hold the full decision logs; ask and I'll send the password.

Andrew Brinkman, 2026Aurora, Colorado