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.

This position is for an existing vacancy.

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 Roor’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

Compensation Band: $250,000.00 CAD OTE

🏠 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

🤝 Perks:

• We host an annual company retreat with great team building activities

• Ample learning and development opportunities to continue growing your career

• Home office setup stipend

• Internet and phone allowance

• Remote first culture

• Weekly Friday paydays!

🤖 AI Notice

At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.

Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too.

And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️

⚠️ Important Notice

We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls.

To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers.

If you receive any suspicious messages or have questions, reach out to us at [email protected].

Your safety and security are important to us — thank you for your vigilance!

Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.