Customer Success Team Lead

We’re looking for a Customer Success Team Lead to join Topline Pro and help shape the future of our customer experience. This is a unique opportunity to step into a true player coach role where you’ll both lead and directly contribute, guiding a small team in a call first, high touch environment while ensuring every customer interaction is consultative, strategic, and impactful.

This is not traditional enterprise customer success. Our customers are small business owners, and engagement is frequent, advice driven, and execution focused. Success in this role means building a team that knows how to prioritize effectively, move quickly, and drive measurable impact across retention and growth.

To set you up for success, your first three months will be hands on as an individual contributor. You’ll operate as a Customer Success Manager, manage your own book of customers, learn the product deeply, and internalize our operating model before formally stepping into full team leadership ownership.

If you’re data driven, thrive in fast paced environments, and want to make a measurable impact on retention and expansion, this role will put you at the center of building an exceptional and durable customer journey.

• Lead a small customer success team while still contributing as an IC.

• Drive customer engagement in a call-first environment, ensuring conversations are high-quality and consultative.

• Run team rituals (stand-ups, reviews) anchored in performance data and activity trends.

• Coach team members on call quality, data use, and customer strategy.

• Re-plan priorities quickly in response to evolving customer needs and insights.

• Partner cross-functionally with Sales, Marketing, and Product to align on customer health.

• Track and improve core success metrics: NRR, GRR, churn, response times, reactivations, and downgrades.

• 5+ years of customer success or customer experience background.

• 1+ years of direct people management experience.

• Proven success operating in a high-activity, phone-first environment.

• Strong data-driven mindset; comfortable analyzing metrics and coaching from data.

• Excellent communication, organization, and problem-solving skills.

• Ability to balance hands-on execution with emerging leadership responsibilities.

• A player-coach who thrives in both doing the work and leading others.

• Energized by a call-first, customer-centric culture (but understand this isn’t a call center).

• Naturally analytical — you use data to prioritize, measure, and continuously improve.

• Adaptable and resilient in fast-paced, evolving environments.

• A team-builder who creates clarity, trust, and accountability through lightweight systems.

• Excited to make a direct, measurable impact on customers and the business.

• Recruiter Screen

• CX Team Lead Screen

• Hiring Manager Screen

• Onsite

• Cofounder Screen

• $100K salary + bonus + equity ($120K+ OTE)

• Full Medical, Dental, and Vision Health Coverage

• Computer and workspace enhancements

• 401(k) plan (non-matching)

• Unlimited vacation, 9 company holidays, including election day, and 1 personal volunteer day a year

• Company-paid Wellhub membership for fitness and wellness

• Dinner covered with Uber Eats + a stocked kitchen to keep you fueled

• Opportunity to take on significant responsibility and ownership in scaling a product that can change the lives of home service pros

• No Bullsh*t: We create meaningful results for our customers and drive growth for our team—ensuring progress and impact are felt every day. Our focus, both internally and externally, is on delivering genuine value rather than superficial solutions or benefit without purpose.

• Think Big, Learn Fast: We move quickly, acting on data to uncover insights and solutions. We embrace risks, knowing every experiment fuels growth—even when it doesn’t go as planned.

• One Team, One Dream: We tackle challenges together with creativity, and an open mind—always seeking solutions and embracing fresh ideas to win as a team.

• Empower Every Voice: We welcome diverse perspectives and bold ideas, creating space for authenticity and respect—because great ideas come from everywhere.

• Be an Owner: We take responsibility for outcomes, act in the company’s best interest, and treat every dollar as our own. We move with urgency, think long-term, and take pride in driving impact.

• Boom!: We take time to celebrate each other’s achievements, big and small—at work and in life—because shared success fuels lasting momentum. And we end all team meetings in a “Boom!”

We're building an AI-powered Shopify for service businesses. We help service pros (e.g., roofers, landscapers, painters, cleaners) acquire direct business, fast. Up and running within minutes using Gen AI, our digital storefront products help pros get discovered, trusted, and booked repeatedly.
Topline Pro was co-founded by Nick Ornitz (CEO) and Shannon Kay (COO), with an excellent team of 120+ rockstars and plans to expand further in 2026. We serve thousands of local service businesses and were named one of the top 50 Tech Companies building for SMBs in 2023 and 2024.
We're YC-backed and well-funded, with several years of runway, and we've experienced rapid growth over the past year. We're in a phenomenal position to scale, with the financial foundation, product-market fit, and momentum to go big. You'll be joining at an inflection point, where the groundwork is laid, and the path to massive impact is clear.
We believe "great candidates" do not come about simply from a check mark next to past experience. We believe in hiring people, not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply.
Topline Pro is committed to building an inclusive workplace and assembling a team from diverse backgrounds. We ensure that individuals with disabilities receive reasonable accommodation throughout the application and interview process. We strongly encourage applications from underrepresented candidates and those from nontraditional backgrounds.