AI can do a lot. I make sure it makes you more human, not less.
Hi, I'm Jess. Right after a raise, the founder is still closing every deal, onboarding lives in one person's head, and support is a shared inbox nobody owns. I come in for a few days a month and set up the whole customer side with you, from first lead to renewal. AI takes the notes, the follow-ups and the busywork. Your team gets their time back for what customers actually remember: a real person who knows them.
Every stage, from first lead to renewal, gets an owner, a playbook and a number you can watch.
I've built this before, at a booking company that went from startup to Booking Holdings.
Pick the piece that hurts most right now.
Sales and AI Setup Sprint
30 daysFor founders still running every deal themselves.
- CRM cleaned up, pipeline stages defined, a forecast you can trust
- A written sales process and playbook your first reps can follow
- AI workflows for prospecting, follow up and call notes that still sound like you
Onboarding and Customer Success Build
4 to 6 weeksFor teams signing customers faster than they can get them live, and keep them happy.
- A repeatable onboarding program with clear handoffs from sales
- A support desk that works: ticket routing, response times, an AI first reply and a help center
- Health scores, check-in rhythms and an early warning list before anyone churns
- A renewal and upsell rhythm, so happy customers turn into more revenue
AI Operations for your team
2 to 4 weeksFor companies that bought AI tools and want people to actually use them.
- The right AI setup for each team, with simple usage rules
- Your brand voice built in, so nothing goes out looking like another generic AI flyer
- Hands-on training and a playbook of everyday workflows
- Time saved measured, so you know it's working
Fractional Head of Sales Ops
Ongoing, a few days a monthFor when you need a senior operator, not a full-time hire yet.
- Hiring plans, ramp plans and coaching for your first sales and success hires
- Weekly pipeline and forecast review with the founder
- Keeps the systems above running as you grow
From first call to a customer team that runs without you in the room.
- Day 1
Intro call
20 minutes. What's working, what's breaking, what the raise needs to buy you.
- Week 1
Audit
I look at your pipeline, CRM, onboarding and tools, and hand you a short plan.
- Weeks 2 to 4
Build
I set it up with your team, inside the tools you already pay for.
- Handoff
Run it
Playbooks, training and dashboards, so your team owns it from here.
Small teams with fresh funding and a founder who's still selling.
Good fit
- Seed to Series A, about 10 to 60 people
- Vertical SaaS, booking and scheduling software, marketplaces
- Fitness, wellness, hospitality and other small business markets
- US based, happy to work remotely
What you get
- Someone who has carried a quota, run a region and built the playbooks
- Systems your next hires can learn in weeks, not months
- AI that gives your team hours back for customers, never a bot pretending to be you
- Someone who's not anti-AI, just anti-lazy-AI
Yes, I have a lot of tattoos. No, I won't take the beanie off for the board meeting.
I've spent 12+ years helping companies sell better and keep their customers happy, mostly at booking software that grew up fast. I'm a big-company playbook person with a small-startup tolerance for chaos. I live in the White Mountains of New Hampshire and work remotely with teams all over the US.
- The early daysAssistant field hockey coach, Tufts UniversityTurns out coaching is just sales enablement with more running and better snacks.
- 2015 to 2022FareHarbor (Booking Holdings)Walked in as a Senior Account Executive. Became Division Sales Manager, then VP of Sales Operations and Enablement, where I cut new hire ramp from 15 months to 8. Then I moved to Amsterdam to run EMEA as General Manager and made the team 34% more efficient while COVID shut down the entire travel industry. Fun times.
- BevSpotChief of StaffGot sales, onboarding and success rowing in the same direction, and cut onboarding time in half with AI.
- 2021 to nowConsultant to startups and scale-upsSales hiring, onboarding and the processes nobody has time to write down.
- NowFounder, InINKA booking platform for tattoo artists. Yes, the tattoos count as market research. I run its sales on AI workflows I built myself, which is how I learned exactly where AI helps and where a human has to step in.
- Off the clockCrossFit coach and runnerYou'll find me coaching an early class, out on a long run, or walking my dog Athena. Probably in the beanie.
Tell me what's breaking.
No deck, no 12-step sales funnel. Send me a couple of lines about where things are after the raise and I'll write back myself, usually the same day. If I'm not the right person, I'll tell you who is.