Director of SMB Sales

HoneyBook is the leading AI-powered business management platform for service-based business owners. Designed to enhance - not replace - independent professionals. HoneyBook’s AI-powered tools help businesses attract leads, connect with clients, book projects, and manage payments more efficiently. With AI seamlessly integrated into every workflow, entrepreneurs can focus on their craft while scaling their businesses with confidence. Since its founding in 2013, HoneyBook has powered over 25 million client relationships and processed more than $12 billion in transactions, helping independent businesses grow faster and smarter.

Our culture is built on five core values that inform everything we do. We encourage collaboration, feedback, ownership, and maintain a growth mindset. We know experience comes in many forms - some visible on your resume, others not. No one candidate will be a 100% perfect match to our description, so if you thrive in a fast-paced, intellectually curious environment and have relevant experience, we encourage you to apply.

The best sales leaders don't wait for the lead to go cold, they're already on the phone. We're 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. A warm lead sitting untouched for an hour is a lost deal in your mind.

You're joining at the ground floor of a sales motion we're building in earnest. That means 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