Director of SMB Sales

About the role

HoneyBook is looking for a Director of Sales who owns revenue like it’s their own business. You’ll build the systems, hire the team, and set the pace, and you’ll do it while personally modeling the hunter mentality you expect from your reps. You’re joining at the ground floor of a sales motion we’re building in earnest: the CRM isn’t clean yet, the pipeline definition doesn’t exist yet, and forecasting isn’t happening yet. You won’t inherit a finished machine—you’ll build it, while still hitting the number. And you’ll build it AI first: every process you stand up should assume AI does the first pass, your reps and you included.

What You’ll Do

• Own the revenue number with full accountability for pipeline coverage, forecast accuracy, and close rate.
• Build a clean, disciplined CRM: clear deal definition (not every trial or touch is a deal), standardized stages, mandatory amounts and close dates, and clean pipeline hygiene your whole team follows without you chasing them.
• Launch a real forecasting motion in partnership with Finance: monthly commit, best case, and pipeline coverage against target.
• Bring AI into the sales motion itself: lead scoring, qualification, call prep, follow-up drafting, forecasting support, pipeline hygiene checks. If a task can be AI-assisted, you default to building it that way.
• Hire and onboard 2+ AEs and build the ramp plan, hiring bar, and coaching cadence that gets them producing fast.
• Instill urgency as a team standard: warm leads get called immediately, no-shows get re-booked within 48 hours, deals don’t sit untouched.
• Improve win rate through real diagnosis of where deals are lost (stage, reason, source), not just top-down pressure to close more.
• Run a weekly pipeline review that surfaces real numbers: total pipeline value, weighted pipeline, deals closing this month, stage conversion rates.
• Coach reps on both pipeline discipline and deal execution, raising the bar on activity and quality at the same time.

What We’re Looking For

• AI-first mindset. You reach for AI tools by default, not as a novelty. You’ve used AI to speed up prospecting, call prep, follow-up, or reporting, and you expect your team to do the same.
• 5+ years in sales leadership, with direct experience owning a revenue number.
• Proven hunter instinct: track record of building or scaling an outbound motion, not just managing inbound flow.
• Hands-on CRM fluency (HubSpot preferred): you’ve built or fixed pipeline stages, deal definitions, and reporting from scratch.
• Experience forecasting with Finance: commit/best case methodology, pipeline coverage ratios, cadence.
• Track record hiring and ramping AEs, with a clear point of view on what a strong hiring bar looks like.
• A bias for speed: you believe a lead called in the first hour converts differently than a lead called the next day, and you build your team’s habits around that belief.
• Excellent communicator, direct in feedback, clear with data, and comfortable bringing recommendations (not just options) to leadership.

Exceptional Candidates Will Also Have

• Experience working for a business with two-fold revenue streams: subscriptions and transactions.
• Background selling into venues, hospitality, or small business/creative verticals.

The Good Stuff

• Mission-driven: You’ll be joining more than just another startup. Our members’ success is at the heart of everything we do.
• Impact: We move quickly and encourage every employee to push the envelope. Our best ideas come from out-of-the-box thinking and innovation; be ready to fail fast and often!
• Compensation: We offer a competitive salary and meaningful equity grants.
• Benefits & perks: From wellness programs to exceptional family leave policies, the health and happiness of our employees are foremost.

Our Core Values

• People come first: We prioritize people as we explore opportunities and work through challenges.
• Raise the bar: We push for greatness—for ourselves, each other, and our members.
• Own it: Trust and ownership let us make decisions with confidence.
• We love what we do: We bring passion to our work and love what we create for our members.
• Keep it real: Authenticity, respect, and transparency are at our core.