About Our Client

Our client is rapidly growing and building the financial back office for therapists. They are seeking a Director-level (or rising) sales leader to help them write their next chapter of growth: from $10M to $25M+ in ARR. This is not a “maintain the engine” role, but a build, fix, and grow role for someone who thrives in motion, wants full ownership, and sees ambiguity as opportunity.

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About The Role

This is a rare opportunity reporting directly to the President, partnering with Product, Marketing, and Ops, and shaping the entire sales motion. It’s an opportunity for someone who’s either done it before or is ready to do it now who knows what great looks like, but wants the autonomy and leadership to make it their own.

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You’ll be the one setting the calendar, clarifying expectations, refining talk tracks, and reviewing the pipeline line-by-line. That’s the job. You’ll be both coaching and closing not forever, but for now because the team is at that inflection point where leadership isn’t about stepping back, but stepping in, and building the path to scale for this organization alongside a team of skilled, capable more senior full-cycle reps.

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What you'll own:

• Lead the sales strategy and execution through its next growth chapter — from $10M to $25M+ in ARR.
• Manage and grow the existing team of 7 inbound ISRs — coach them, raise the bar, and build the next layer of leadership as the company scales.
• Shift the sales engine from 100% inbound to a blended inbound + outbound model — design the motion, test the tactics, and build the process that scales.
• Own full-cycle rep performance — hiring, ramping, comp, enablement, and retention — and hold the line on outcomes.
• Be a strategic partner to sales, marketing, product, and operations — align on ICP, shape offers, and drive GTM cohesion.
• Drive operational discipline — weekly team structure, forecast cadence, 1:1s, call reviews, and hygiene rituals that build trust in the number.
• Rewrite the playbook — and then keep rewriting it — with sharper talk tracks, stronger frameworks, better objection-handling, and clear conversion paths.
• Help define what excellence looks like across every stage of the funnel — from first touch to signature to onboarding handoff.

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This role is for you if:

• You’ve scaled a sales team through the early growth stage before — from $10M to $25M+ in ARR — or you’ve been a top-performing sales leader ready to take the reins of your own department and own the number.
• You’ve sold into SMBs in fast-moving, high-consideration sales environments — ideally in healthcare, financial services, or vertical SaaS — with ACVs between $2K and $10K and sales cycles under 20 days. You know how to balance volume and thoughtfulness.
• You’ve led a team of full-cycle reps, not just SDRs or closers, and you’ve carried a team quota of $5M+ and hit it. Not by luck — by running tight process, creating a culture of high accountability, and making your team sharper every month. You’re comfortable, and hungry to grow teams, scale geos, and test into new verticals.
• You know what it takes to build the outbound engine from scratch. The hiring company has built a repeatable inbound funnel and you will help them move from a 100% inbound “catch” motion to a hybrid motion where reps are trained to hunt, not just wait on the top of the funnel to do the work for them.
• You’ve worked cross-functionally with Product and Marketing — you know how to push on ICP, shape positioning, challenge pricing, and influence roadmap. You don’t wait to be told what you need — you ask, push, and bang the table if needed.
• You’ve built comp plans, forecast models, activity systems, and scorecards — and you know where to start and what can wait. You’ve seen the mess before, and you know how to make it simple again.
• You pride yourself on leading from the front — joining calls, listening to recordings, refining scripts weekly, giving your reps the tools to succeed. You don’t outsource accountability. You set the tone and drive the standard.
• You care deeply about the craft. You want to win, yes — but you also want to build a sales org that is respected inside and outside the company. A team that earns trust, doesn’t cut corners, and is proud of how they show up for their customers.

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What is being offered:

• A high-impact, senior leadership (non-executive) role at the table with real ownership and decision-making power to influence the trajectory
• A company with strong product-market fit, thousands of paying customers, and a strong growth trajectory with line of sight to profitability, and strong runway
• Full executive support to scale the team and invest in tools, headcount, and outbound (this is an expectation!)
• Competitive compensation, meaningful equity, and with success a path to promotion over time
• Comprehensive health benefits including a monthly wellness stipend
• A mission-driven culture grounded in helping therapists build sustainable, independent practices.

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Why this role matters:

• This role is a force multiplier. If the team gets it right, it unlocks growth across the business: stronger revenue, clearer positioning, better product signals, and tighter customer feedback loops. The company will grow faster, more predictably, and more profitably — not because headcount was added, but because the team made it work.
• This is the kind of role where the right person can change the company’s trajectory — and where the company can change their trajectory, too.

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Note:

“We are not the EOR (Employer of Record) for this position. Our role in this specific opportunity is to connect outstanding candidates with a top-tier employer. Swooped helps candidates around the world to discover and stay focused on the jobs they want until they can complete a full application in the hiring company career page/ATS.”