Director of Expansion Sales

Role Overview

• Design and operationalize a layer-cake expansion strategy across: Self-serve / product-led expansion: in-app upgrades, usage-based triggers, paywalls; Sales-assisted expansion: SMB/MM account growth; Enterprise/strategic expansion: multi-product, multi-team, multi-year growth
• Define segmentation, triggers, and handoffs between product, CS, and sales
• Build playbooks for upsell, cross-sell, add-ons, and usage expansion
• Own NRR, expansion ARR, expansion pipeline, and expansion conversion rates
• Build and manage forecasting models for expansion revenue
• Partner with RevOps to implement dashboards, attribution, and pipeline visibility
• Partner with Product and Growth to embed expansion into the product experience
• Define PQLs, usage signals, and upgrade triggers
• Build a seamless product-led to sales-led conversion motion
• Inherit and lead a high-performing Expansion team (Account Managers)
• Establish hiring plans, comp structures, and career paths
• Coach managers and ICs on consultative expansion, value selling, and account strategy
• Partner with the following departments and act as the internal expert on expansion best practices in PLG SaaS: Product Growth on packaging, pricing, and feature gating; Marketing on lifecycle, nurture, and expansion campaigns; Customer Success on adoption, health scoring, and expansion readiness; Finance on pricing strategy and revenue modeling

Requirements

• 8–12+ years in B2B SaaS revenue roles
• Experience in SMB-focused SaaS with high velocity PLG motion
• Proven success in a PLG environment with product-led and sales-led motions
• Direct experience building or scaling expansion / upsell/cross-sell programs
• Experience owning NRR, expansion ARR, and forecasting
• Demonstrated success in leading and developing quota-carrying teams
• Deep understanding of layer-cake / multi-motion GTM models
• Strong experience with usage-based or hybrid pricing models
• Familiarity with PQL frameworks, lifecycle marketing, and product analytics
• Experience working with RevOps and data tools (e.g., Salesforce, HubSpot, Snowflake, Looker)

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