Leadership from the trenches.
AI as the second chair.
Revenue as the byproduct.
I lead enterprise sales teams in the deals every day. The AI systems I build are the second chair, pulling weight on the work that doesn't need a human, so the team can focus on the work that does.
The Second Chair doctrine
Trenches. Second chair. Byproduct.
An operating model for sales leaders in the AI era. The job used to require three roles — the closer, the coach, and the ops architect. Now it requires one operator who runs the loop, with AI as the second chair. Tested across $12M+ in enterprise pipeline.
A sales leader who can't close can't coach. I run the hardest deals myself, document the moves, then turn them into the system. Leadership is reps, not slides — and reps create the data the second chair learns from.
This quarter: ran the top 3 enterprise deals myself. The patterns became the deal-coach prompt.
AI isn't a tool you deploy — it's a teammate that pulls weight. The systems I ship are second chairs for specific work: deal coaching, signal triage, forecast calibration, rep ramp. Each one removes work that didn't need a human in the first place.
This quarter: killed the volume-cadence playbook after the signal-cadence second chair beat it 3x.
Teams that chase revenue directly miss it. Teams that build the system — sharp qualification, real coaching, AI leverage on the noise — produce revenue as the natural output. 75+ reps coached, 80% reached top performer within 9 months. The number followed the system.
This quarter: forecast confidence on top 10 deals +18pts. We didn't chase the number — we closed 4 EB gaps.
A working library of second chairs, shipped.
Internal tools built for the seats I've held — territory hubs, pipeline cockpits, qualification scorers, governance dashboards. Each one closes a loop a rep or leader was running by hand.
→ live internal tooling · names and chrome generalized for public view
The deal coach I built for my team.
A live working demo. Pick a deal scenario. The second chair reads the signals and tells you the next move — the same analysis I run with my reps before every forecast call.
Revenue built. Systems that made it possible.
Five revenue functions. Three built from zero. Each one a closed loop: lead from the trenches, document the moves, build the second chair, scale the team. Then do it again, faster.
Lead enterprise SDR and AE teams across two regions. Own multi-million new business target. Built the deal coaching infrastructure that lifted rep prep time 40% and connect rates 2.6x. Currently in seat.
Inherited a stalled GTM. Rebuilt the sales motion, implemented MEDDPICC across the team, shortened cycles 20%, raised average deal size 150%. Hit 173% to quota two years running.
Built the entire Customer Success and Account Management function from scratch with full P&L ownership. Drove net revenue retention to 113% and cut churn in half within four months. Scaled the team 250%.
Closed enterprise into Fortune 500 retail, consumer tech, and remote workforce platforms. Exceeded Q4 forecast by 40%. Expanded the customer base by 150 accounts during tenure.
Four promotions in four years. Ranked #1 of 60 SDMs company-wide. Authored the customer success playbook distributed to 90 CSMs across the org. Where the operator habits were forged.
The systems behind the numbers.
Every second chair is built for a specific seat. Some coach the AE through a stalled deal. Some triage signals before a forecast call. Some ramp a new hire in weeks instead of months. The leverage is in the specificity.
Real-time deal scoring integrating Gong, Clari, ZoomInfo, and Outreach signals. Surfaces the next move for every rep on every deal — the same logic the live demo above is built from.
SDR dialer pairing live AI coaching with account-specific signals at the moment of first contact. The rep gets the right opener, the right hook, the right reason to call — before the line picks up.
Whitespace mapping and account expansion intelligence. Built as a hiring leave-behind for a Director of Channel Sales interview process at a cybersecurity firm. The work that closed the interview.
Pattern matcher that scores every open deal against historical wins and losses of similar shape. Tells the team not just where the gap is — but which gap to close first based on which deals like this actually closed.
What I'm working on, this week.
A running record of what's shipping, what's working, and what I'm killing. Sales leaders should publish their process the same way engineers publish their commits.
What the next 24 months look like from the deal floor.
The best revenue orgs aren't replacing their stack — they're compounding it. Agents on top of the CRM, AI in the call, internal tools shipped in days, forecasts that update themselves between Mondays. These are the bets being placed now — half of them already shipped in the shelf above.
Salesforce shipped Agentforce, HubSpot shipped Breeze, Rippling and Ramp are wiring agents directly into their own data. The best orgs aren't ripping out the system of record — they're putting an orchestration layer on top of it so the rep works in one surface and the CRM stays clean as a byproduct. The read-and-write layer is already running inside the second chair.
Recording and scoring are table stakes now — the best teams already run them. The next layer is live in the call: objection routing, champion-silence detection, next-best-question whispered to the rep, full account context held in memory. It doesn't replace the AE; it makes a good AE look like a great one and a great AE unmistakable. The signal-cadence chair is the v0.
Look at how Ramp, Rippling, and the top-decile RevOps orgs run: internal tools shipped in days, not quarters, owned by the operators who use them. Lovable, Cursor, and Claude Code make that the new baseline. Every second chair on the shelf above started as a Friday afternoon project. The leaders who ship pull further ahead of the ones who file tickets every month they don't.
The best CROs aren't killing the forecast call — they're walking into it with a deal-state agent that already updated the number between Mondays. MEDDPICC scoring, deal inspection, next-step nudges, slip risk — all running continuously against the same surface the CRO trusts. The meeting goes from reconstruction to decision. The ritual survives; the theater doesn't.
Currently writing.
Drafts in progress. Published when they're sharp enough to be useful — not on a content calendar.
In the deals. Building the second chair.
I'm open to sales leadership at companies serious about the AI-native motion. Also open to advisory engagements with sales orgs building their own second chairs, and conversations with operators who think the next decade of sales leadership looks nothing like the last one.
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