Roofr

Director of Expansion Sales

Roofr

full-time

Posted on:

Location Type: Remote

Location: Canada

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Job Level

Lead

About the role

  • 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.
  • 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.
  • 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.
  • 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.

Requirements

  • 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
Benefits
  • 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
  • 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!
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
B2B SaaSaccount managementsales leadershipnet revenue retention (NRR)expansion revenuecustomer segmentationforecasting modelsaccount planning frameworkscommercial negotiationvalue realization
Soft Skills
cross-functional collaborationleadershipcoachingstrategic planningdata-driven mindsetadaptabilitycustomer engagementteam developmentcommunicationproblem-solving