Director of Expansion Sales

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products. We have an amazing culture, strong financials, and best‑in‑class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact. We’re looking for a strategic and highly experienced Director of Expansion Sales to build, scale, and lead Roofr’s direct sales organization. This leader will proactively drive Roofr’s revenue motion for our existing customer base, including expansion, upsell, cross‑sell, and account growth, with a strong emphasis on building a repeatable, high‑velocity expansion engine. This role requires someone who has “been there, done that” at a high‑growth B2B SaaS startup, thrives in a fast‑paced environment, and knows how to operationalize revenue motions using a layer‑cake model, customer segmentation, and a structured playbook approach. If you are a data‑driven, customer‑centric sales leader who knows how to hit plan, balance customer value with revenue outcomes—and build and scale multiple customer‑facing sales teams from the ground up—we’d love to meet you. You’ll have an opportunity to: Leadership & Strategy Build, lead, and scale Roofr’s direct sales team. Develop the long‑term strategy aligned with Roofr’s expansion revenue motion, upsell, retention, and customer engagement goals. Design, implement, and operationalize a layer‑cake model and customer segmentation framework to optimize touchpoints across customer tiers and drive consistent expansion outcomes. Partner closely with CX, Partnerships, Product, RevOps, and Marketing to ensure seamless customer handoffs and a unified customer journey. Drive our customer‑facing culture across teams, ensuring leadership stays close to the frontline and directly engaged in key deals and customer conversations. Revenue Ownership Own net revenue retention (NRR), expansion ARR, and account growth KPIs across the existing customer base. Drive high‑impact expansion and upsell programs that deliver meaningful revenue growth—especially through a repeatable, high‑volume sales motion. Build forecasting models, renewal processes, and account planning frameworks in partnership with RevOps. Establish rigorous and repeatable account review cadences and strategic QBR frameworks to drive outcomes and accountability. Partner with Sales leadership and RevOps to define team quotas and ensure teams are consistently executing against hard revenue targets. Team Development & Enablement Recruit, hire, and develop high‑performing sales people. Create scalable processes, playbooks, enablement materials, and performance metrics aligned to expansion revenue goals. Coach teams on strategic account planning, value realization, and commercial negotiation, with a consistent focus on converting customer engagement into upsell/cross‑sell outcomes. Operational Excellence Partner with RevOps to refine compensation plans, territory alignment, and customer segmentation. Implement tooling, dashboards, and workflows to increase efficiency and predictability across the expansion motion. Identify gaps in the customer lifecycle and proactively design solutions to improve adoption, retention, and expansion conversion. What you’ll bring to the role: 7+ years in B2B SaaS account management and/or sales leadership, with at least 3+ years leading revenue teams at a high‑growth startup. Proven success owning NRR, renewal, and expansion revenue targets, including managing teams against hard quotas. Experience building and scaling customer‑facing teams from early stages, including managing through team leads and/or managers. Expertise operationalizing layer‑cake, segmentation, and high/low‑touch customer engagement models to support repeatable revenue outcomes. Strong background in expansion + upsell motions, commercial negotiation, and value realization strategies. Data‑driven mindset with the ability to forecast accurately and build scalable processes. Exceptional cross‑functional collaboration skills and experience partnering with Product, Sales, CS, and RevOps. Ability to thrive in a fast‑paced, ambiguity‑heavy, high‑growth environment. Bonus Points: experience as a Revenue leader within a PLG environment What we offer (US + Canada) When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career: ️ Vacation/Paid Time Off: 1st week of employment is mandatory PTO Start your journey with Roofr by decompressing and recharging - we will see you in week 2 1 Friday off per month (we call those our laundry days) Company wide paid shutdown for the week between Christmas and New Years Flexible time off 80% employer‑paid benefits in the U.S. and 100% employer‑paid premiums for Extended Healthcare and Dental in Canada RRSP/401k match Generous Parental Leave policy