Expansion Team Lead at Hearth in Remote

The Opportunity

Hearth is in the middle of an aggressive push to attach its AI product, Harper, to the existing customer base. Harper started as an AI Receptionist that answers calls, blocks spam, books estimates, and follows up via text. It's rapidly evolving into a full business operations platform: AI-composed messaging, social media content creation, automated lead follow-ups, and more.

As Expansion Team Lead, you'll own the team responsible for selling Harper to Hearth's existing 10,000+ contractor customers. You'll manage a team of 3-5 Expansion Reps, driving close rates, coaching reps on calls daily, and partnering with Marketing, Sales, and RevOps to build the pipeline that feeds the team.

This role sits at the center of Hearth's AI revenue growth motion. The Expansion team is the primary engine for converting existing financing customers into AI customers, and AI adoption is Hearth's top strategic priority.

• Direct revenue ownership: You and your team are the primary driver of AI attach rate across Hearth's existing base. Your performance directly moves the company's most important metric.
• Rapidly evolving product: Harper adds new capabilities every few weeks (social media creator, AI messaging, automated follow-ups). Each new feature gives your team a fresh reason to call and a stronger value proposition to sell.
• Real coaching leverage: You'll have call intelligence tools (Attention scorecards, AI-powered call analysis) and AI role-play software (Avarra) to identify exactly where reps are losing deals and coach them with precision.
• Cross-functional visibility: You'll work directly with executive leadership, Sales, Marketing, RevOps, and Product in weekly revenue syncs. This role is high-visibility and high-impact.
• Mission-driven selling: When a contractor activates Harper, they stop missing calls and start booking more jobs. The ROI is immediate and tangible for small business owners.

What You’ll Do:

Lead and Develop the Expansion Team

• Manage a team of 3-5 Expansion Reps, owning their ramp, daily performance, and professional development.
• Run daily coaching sessions using call recordings (Attention), scorecard data, and AI role-play tools (Avarra) to sharpen discovery, objection handling, and closing skills.
• Own and iterate on the team's script and demo flow. The product evolves constantly, so the pitch needs to evolve with it. Identify what's working on top-performer calls and package it for the team.
• Set clear performance expectations and hold reps accountable. Run weekly 1:1s, pipeline reviews, and performance conversations. Manage the PIP process when needed.
• Step in on escalated opportunities when needed: second-voice calls on stalled deals, manager callbacks, and recovery on leads that need a stronger push. Your job is to unblock deals, not carry a personal quota.
• Hire and onboard new Expansion Reps as the team scales.

Drive Close Rate and Pipeline Performance

• Own the team's close rate as the primary metric. Diagnose where deals are dying (discovery, demo, pricing, follow-up) and implement fixes weekly.
• Partner with Marketing (lifecycle campaigns, SMS sends, email nurtures) to ensure the team has a steady flow of qualified leads. Coordinate on send timing, audience targeting, and lead handoff processes.
• Partner with the SDR/Prospect team on demo quality, demo set rate, and no-show follow-up processes.
• Manage live transfer volume from CS and Support teams: enforce transfer quality, coach those teams on what qualifies as a warm transfer, and ensure speed-to-lead on inbound hand-raises.
• Track and report on key metrics weekly: demos held, close rate, deals per rep per day, ARR per rep per day, AI attach rate, activation rate, and pipeline coverage.

Consultative Selling and Product Positioning

• Ensure every rep can run strong discovery: uncovering missed-call pain, quantifying lost revenue, and connecting Harper to the contractor's specific business challenges.
• Position Harper's evolving capabilities (call handling, SMS follow-ups, social media content creation, AI messaging, lead follow-ups) as an integrated business operations platform, not just a receptionist.
• Ensure the team uses the ROI calculator on every demo and ties the price to concrete dollar-value impact (one missed call per week at $10K+ average job value).
• Coach reps on common objections: monthly pricing concerns, "I already have a voicemail/answering service," call forwarding setup anxiety, "I'll wait until busy season," general tech discomfort.

Partner Cross-Functionally on AI Revenue Growth

• Participate in weekly AI Revenue Team syncs with Sales, Marketing, SDR, CS, and executive leadership.
• Surface product feedback and customer friction to Product and Engineering. When contractors consistently struggle with onboarding, activation, or specific features, you're the voice that escalates it.
• Coordinate with the AI CS/Onboarding team to ensure closed deals activate quickly. Speed from sale to go-live directly affects retention.
• Test and iterate on new lead sources and campaigns with Marketing (SMS blasts, winback sequences, social media creator hooks, DPC re-engagement, email nurtures).

What We’re Looking For:

You've managed a small sales or expansion team before and you know what it takes to move close rates. You're the kind of leader who listens to 10 calls a day, spots the moment a rep accepts an objection too quickly, and turns that into a coaching session the next morning. You've built or iterated on scripts, run role-plays, held reps accountable to metrics, and made tough calls when someone isn't performing.

You understand the craft of selling because you've done it yourself, but your focus now is multiplying the output of your team. You'd rather make three reps 20% better than close a deal yourself. You know how to diagnose whether a problem is a coaching issue, a pipeline quality issue, or a process issue, and you fix accordingly.

You're comfortable in a fast-moving environment where the product, the script, and the lead sources change week to week. You don't wait for perfect processes. You build them as you go and iterate based on what's working.

• 2-4+ years of sales experience, including at least 1 year managing or leading a small sales/expansion team (3+ direct reports).
• Demonstrated track record of improving team close rates through coaching, script development, and accountability.
• Experience building or iterating on sales playbooks, talk tracks, and enablement materials.
• Experience running high-velocity sales motions: multiple demos per day, short sales cycles, fast follow-up.
• Comfortable managing reps who sell to non-technical SMB buyers in phone-heavy environments.
• Experience using a CRM (Salesforce preferred) and call intelligence tools (Attention, Gong, or similar).

Preferred

• Experience selling AI, SaaS, or technology products to small businesses.
• Experience in home services, trades, fintech, or vertical SaaS.
• Experience with AI-powered coaching tools (Avarra or similar) and structured role-play programs.
• Familiarity with expansion/upsell motions within an existing customer base (vs. net-new only).
• Experience partnering closely with Marketing on lifecycle campaigns and lead generation.

Our Core Values

• Truth. We value honesty and data. We seek to understand what is reality, so we can effectively respond to it.
• Slope. Rate of change over time. We hire and reward based on a team member’s potential, capacity, and growth-mindset, rather than a fancy resume. 
• Mutual Benefit. The best outcomes happen when everyone wins - customers, team members, and the company. We seek to understand each other’s aspirations and create alignment to get there. 
• Competitive Greatness. We desire an opportunity and environment from which to pull the greatest versions of ourselves out into the world, rather than just a “job”. 

Benefits:

• Mission-driven, values-based culture.
• Competitive pay.
• Unmatched opportunities to learn and develop; front-row seat at a fast-growing tech startup
• Generous PTO, plus paid company holidays.
• Stock options.
• Medical, dental, and vision options.
• 401(k)
• Free Employee Assistance Program
• Parental Leave Program
• Pet Insurance

Compensation:

• OTE: $150,000–$170,000 (Base + Variable)

The expected compensation range for this position is displayed in compliance with all local/state regulations. The expected compensation range for this position is based on a number of factors, including but not limited to: individual education, qualifications, and prior work experience. The total annual compensation package will consist of a base salary and eligibility to participate in our sales commission structure.

Location

Remote

More About Us

Hearth embraces diversity. We are proud to be an equal opportunity workplace and do not discriminate on the basis of sex, race, color, age, sexual orientation, gender identity, religion, national origin, citizenship, marital status, veteran status, or disability status. We consider for employment qualified applicants with arrest and conviction records.