- Most strategy work ends at the recommendation. Someone else decides whether it was right, usually years later, usually without telling you
- This role compresses that loop to a quarter. You’ll pick a segment of the mid-market, write down why Lightfield should win there, and then find out whether you were right the only way that produces a real answer: by getting companies in that segment to buy
- Here’s the underlying problem. Every generation of CRM invented its own way into the market. Siebel had enterprise sales, Salesforce had the cloud, HubSpot had inbound. AI-native CRM will have its own route, and nobody has mapped it yet. The mid-market is where that map gets drawn, and it isn’t one market. It’s fifty, cut by vertical, by incumbent stack, by how each company sells and who signs. Each segment has a different buyer, a different displacement story, and a different reason to move now
- You will carve it up and run market entries, end to end. Form a thesis about a segment. Open the doors yourself. Run the deals through to close. Own the implementation so the thesis survives contact with reality. When a segment works, codify it into a playbook, hire account executives to run it at scale, and move to the next one. When it doesn’t, kill it in writing, with evidence, and redeploy
- You’ll report directly to the CEO and work out of the same deals. You’ll be measured on logos: named accounts closed in new segments, because early on the question is whether a segment works, not how big the first checks are
- We want to be precise about the shape of this, because the failure mode is obvious from both sides. This is not a strategy seat producing analysis for other people to act on, and it is not an account executive role with a new title. It’s the job of proving markets exist, where the proof is commercial. You will write the segmentation memo and you will also send the first hundred emails into the segment. Both halves are the job. Neither is beneath it
- The arc of the role is the arc of a business: thesis, proof, playbook, team. The person who does this well two or three times hasn’t done a rotation in sales. They’ve built our mid-market business from a blank page, and the natural next step is to run it
- Map the mid-market: segment it by vertical, incumbent stack, and how each company sells, and make the case for where we enter first
- Write one thesis per segment: who buys, what we displace, why now, what a won deal looks like. One page, falsifiable
- Test it in market: build the target list, generate your own pipeline, and run deals through to close, with the CEO alongside you
- Own implementation for what you sell, because a thesis that dies in onboarding was never true
- Codify what works into a playbook a new account executive could run without you in the room
- Kill what doesn’t, fast, in writing, with evidence rather than vibes
- Hire and ramp the team that scales what you proved
Benefits
- Meaningful early equity
- Health insurance (medical, dental, vision)
- 3 weeks of PTO
- 11 paid company holidays + we enjoy a winter holiday break
- Wednesdays work from home
- Regular team dinners, events, offsites, and retreats
- 3 months of paid family leave
- 401k plan
- Other perks include: commuter and lunch stipend
You’ve noticed that the operators you advise or finance are playing a more interesting game than you are, and you want in at the point of maximum leverageYou’d rather be judged by the market than by a review committeeCompetitive drive that shows up somewhere verifiableYou understand that in this job, selling is the research method. You want to do it yourself, not delegate it, and you can explain whyYou think in hypotheses and you write clearly. Your one-pagers get readYou’re structured enough to segment a market rigorously and scrappy enough to cold-email your way into it2 to 5 years at a top investment bank, consulting firm, or investment firm, or an MBA from a top program on top of that record. You’ve owned work that real money moved onYou’re comfortable when there’s no playbook, because writing the playbook is the jobCovered software or worked with SaaS companies as a banker, consultant, or investorYou’ve sold something before: a company, a fundraise, a side business, anything where a stranger said yes to youTime at an early-stage startup, or a founder attempt of your ownEnough familiarity with CRM and GTM tooling to have an opinion in front of a VP of Sales