**20-Person Deals, Year-Long Cycles | Leigh Gross (CRO, Synctera) on Selling to the Blocker, Not the Champion**Leigh Gross runs one of the most complex enterprise sales motions you'll hear about. As CRO at [Synctera](https://www.synctera.com/), the banking-as-a-service platform behind embedded banking and card products for companies like Bolt, Zenoti, and BTG Pactual, his team coordinates deals involving **10 people on Synctera's side, 10 on the customer side, and a sponsor bank in the middle** — across sales cycles that can stretch past a year.Before this, Leigh spent 12 years in fintech sales across student loans, SMB lending, and credit data — all heavily regulated, all incredibly complex. And before *that*, he was a commercial attorney. In this episode, Leigh joins Anthony Enrico to break down what it actually takes to sell when compliance can kill your deal, why you should sell to the blocker instead of the champion, and the hard-won lessons about setting up your GTM foundation *before* you go to market.We get into:* The tripartite sales motion — running three sales processes in parallel (fintech, bank, and matching them together)* Why the sales engineer is the most underrated specialized role in complex deals — and why it's also an implementation tool* How Synctera turned banking-as-a-service launches from *years* into a **3-month** average — and made it their moat* Forecasting in long, complex cycles: the "give-and-get" deal model trick that gets fintechs to share projections early* Why traditional BANT / MEDDPICC didn't fit — and the qualification questions that did* The mid-funnel AI use case nobody talks about: handoff documents, trend analysis across deals, and the ADA tool sitting on top of Salesforce* The "build order" of GTM: why RevOps comes before scaled headcount, and why bad early data costs millions at fundraise* The painful re-engineering project (and pizzas) that comes from skipping RevOps too long* Why **weighted pipeline is the currency of fundraising** — and how to defend it in front of a board* Segment-based planning: treating enterprise, mid-market, and SMB as separate lines of business* How to hire that first enterprise rep — the curiosity, ambiguity-tolerance, and slightly different comp plan* Selling to the blocker: why deals die from people you've never met (especially compliance) — and how to control the process upfront**Chapters**00:00 — Intro: from commercial attorney to CRO of a BaaS platform01:24 — The 20-person deal: what a Synctera sales motion actually looks like03:02 — Forecasting long cycles: the deal model give-and-get05:04 — Why BANT/MEDDPICC didn't fit and what replaced it07:12 — The cast of characters and why sales engineering is non-negotiable11:56 — How compliance complexity became Synctera's moat14:07 — The most underrated AI use case: mid-funnel handoffs and trend analysis18:22 — The ADA tool, Salesforce, and how Leigh actually uses AI as a sales leader20:30 — The build order of GTM: why RevOps comes first26:00 — The painful re-engineering project (and pizzas)29:47 — Why weighted pipeline is the currency of fundraising31:50 — Planning nightmares and segment-based GTM37:43 — Hiring the first enterprise rep: curiosity, ambiguity, and comp design42:20 — Selling to the blocker: why deals die from people you've never met47:07 — Controlling the sales process upfront to surface compliance early**About the LeanScale Podcast**The LeanScale Podcast features candid conversations with go-to-market leaders building, scaling, and rethinking revenue operations in the AI era. Hosted by Anthony Enrico, co-founder of [LeanScale](https://www.leanscale.team/).Subscribe for more conversations with operators building the next generation of go-to-market.#EnterpriseSales #Fintech #BankingAsAService #CRO #RevOps #SalesLeadership #ComplexSales #GoToMarket #Synctera