Director of Expansion Sales
Roofr
San Francisco, CARemote
Job Description
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 are looking for a strategic and execution-oriented Director, Expansion Sales to build, scale, and optimize our layer-cake expansion model within a B2B SaaS, product-led growth (PLG) environment.
This leader will own the full expansion motion across our existing customer base, including self-serve expansion, sales-assisted expansion, and enterprise growth plays, ensuring we maximize Net Revenue Retention (NRR) and customer lifetime value.
You will partner closely with Product Growth, Marketing, Customer Success, RevOps, and Sales to design expansion pathways, optimize conversion, and build repeatable revenue engines.
You'll have an opportunity to own:
Expansion Strategy & Layer-Cake Model
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
Revenue & Performance Ownership
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
PLG + Sales Alignment
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
Team Leadership & Development
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
Cross-Functional Leadership
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
What success looks like:
NRR consistently exceeds target
Expansion becomes a predictable, scalable revenue engine
Clear segmentation and layer-cake coverage across all customer tiers
Strong alignment between product usage signals and revenue outcomes
A high-performing, engaged expansion team with clear career progression
What you'll bring to the role:
Required Experience
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
Domain Expertise
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)
Nice to Have
Background in pricing & packaging strategy
Experience with multi-product platforms or add-on ecosystems
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.
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 are looking for a strategic and execution-oriented Director, Expansion Sales to build, scale, and optimize our layer-cake expansion model within a B2B SaaS, product-led growth (PLG) environment.
This leader will own the full expansion motion across our existing customer base, including self-serve expansion, sales-assisted expansion, and enterprise growth plays, ensuring we maximize Net Revenue Retention (NRR) and customer lifetime value.
You will partner closely with Product Growth, Marketing, Customer Success, RevOps, and Sales to design expansion pathways, optimize conversion, and build repeatable revenue engines.
You'll have an opportunity to own:
Expansion Strategy & Layer-Cake Model
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
Revenue & Performance Ownership
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
PLG + Sales Alignment
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
Team Leadership & Development
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
Cross-Functional Leadership
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
What success looks like:
NRR consistently exceeds target
Expansion becomes a predictable, scalable revenue engine
Clear segmentation and layer-cake coverage across all customer tiers
Strong alignment between product usage signals and revenue outcomes
A high-performing, engaged expansion team with clear career progression
What you'll bring to the role:
Required Experience
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
Domain Expertise
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)
Nice to Have
Background in pricing & packaging strategy
Experience with multi-product platforms or add-on ecosystems
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.