Our mission is to increase the success rate of small businesses. Traditional banking has been a growth limiter rather than a growth enabler for business owners, and we’re changing that. Relay is the all-in-one, collaborative money management platform. We’re building for employer SMBs and their finance function, internal and external, and are focused on delivering a human-centric customer experience. Ultimately, we help SMBs be ‘on the money'.
We are looking for a Sales Enablement Leader to join our rapidly growing Sales team. As our Head of Sales Enablement, your role will be to operationalize excellence across the sales organization. You’ll equip our GTM team with the skills, systems, and insights to consistently drive high-quality sales conversations, accelerate time to value, and win with confidence in a buyer-led market.
This is a high-impact, cross-functional role at the intersection of performance, process, and productivity. You’ll own enablement end-to-end—from onboarding and coaching to AI tooling and playbook execution—helping sellers move fast, learn faster, and sell smarter.
What You'll Be Doing:
🔧 Strategy & Ownership
Define and execute the sales enablement strategy across the full GTM org (AE, BDR, AM, managers)
Own onboarding, skill development, and role-readiness programming at scale
Partner with Sales, RevOps, and Product Marketing to translate GTM priorities into repeatable behaviors
Build enablement systems that scale—via platforms, automation, and embedded intelligence
🧠 Coaching, Training & Performance
Lead rep coaching via call shadowing, live deal support, and performance diagnostics
Build role-specific certifications, manager enablement programs, and internal mobility paths
Translate sales friction into high-impact learning programs that drive conversion, speed, and confidence
🛠️ Tooling & Systems
Operationalize playbooks, objection frameworks, and sales knowledge in Notion, Gong, and Salesforce
Deploy AI tooling to accelerate ramp, personalize coaching, and unlock real-time GTM insights
Measure and report on enablement impact across ramp, attainment, forecasting accuracy, and rep productivity
🤝 Cross-Functional Partnership
Collaborate with Product Marketing on messaging, new product enablement, and vertical plays
Work closely with RevOps on workflow optimization, CRM hygiene, and performance intelligence
Align with CX and post-sale teams to drive adoption, expansion, and lifecycle selling
Who You Are:
2+ years in full-cycle, quota-carrying sales (AE/BDR/CSM/AM) and 3+ years in a sales or revenue enablement function, with ownership of onboarding, coaching, and program design
Experience building enablement functions in high-growth B2B SaaS (especially SMB-focused)
Strong grasp of modern selling: buyer enablement, multithreading, negotiation, value selling
Highly fluent with Salesforce, Gong, Notion, enablement metrics, and sales coaching platforms
Ability to simplify complex systems into clear, engaging enablement assets and experiences
Strategic thinker with a builder mindset—you thrive on turning ambiguity into systems that scale
Bonus Points:
Experience in fintech, payments, or SMB SaaS
Experience with BDR → AE transitions or career pathing
Experience implementing buyer enablement frameworks or collaborative deal spaces (e.g., Accord, Aligned)
Event enablement experience (SKOs, QBRs, product launches)
Our Commitment to You
Competitive salary and meaningful equity: Relay employees are Relay owners, complete with equity and a competitive salary.
Comprehensive health benefits: enjoy full health benefits from day one. We offer flexible Health or Wellness Spending Accounts and medical, dental, and vision coverage for you and your dependents.
Flexible vacation and time off: every team member starts with 15 vacation days and 5 flex days to use as needed, plus an extra week of office closure during the end-of-year holidays so you can take time off to recharge and come back better for our customers.
Parental leave with top-up: we offer 12 weeks off with a 100% salary top-up for all full-time employees, regardless of location, and accessible for all parents: birthing, non-birthing, and adoptive.
Hybrid work environment: we value meaningful collaboration and connection at our Toronto office twice a week, with lunch, snacks, and beverages on us.
Dog-friendly space: can dogs really make you happy and healthy? We don’t know for sure, but since we don’t want to chance it, our office is 100% floof-friendly.
Personal and professional growth: through ongoing feedback, mentorship, and coaching, work with peers and leaders who are invested in your growth and success.
Top-tier equipment: as a Mac-first company, our Toronto offices have everything you need to produce your best work comfortably, from multiple screens to ergonomic seating.
Social connection: we believe in celebrating our wins with two annual company-wide get-togethers, quarterly team events, happy hours, and special events and networking opportunities with industry leaders.
We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take changes, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.
The Interview Process
Stage 1: A 40-minute video call with a member of our Talent team
Stage 2: A 45-minute interview with our Head of Sales
Stage 3: A 45-minute virtual whiteboarding session with two members of our Sales team
Stage 4: A 45-minute values interview with a member of our leadership team
Stage 5: A case study + 60-minute presentation with our sales leadership team
Why Relay Might Be the Perfect Fit For You
You push relentlessly for reinvention: You’re built to constantly ask, “How can this be better?” Change excites you and you drive it.
You crave autonomy: We trust our team with big challenges and the freedom to solve them. If you’re someone who takes initiative, is comfortable taking risks, and seeks input when needed, you’ll find the freedom here empowering.
You own your work: You take pride in your work, follow through on commitments, and feel a deep sense of responsibility for outcomes, not just tasks.
You treat comfort as a red flag: You seek growth. When things feel too comfortable, you lean into change. You’re excited about stepping into the unknown and navigating new terrain to create something better alongside your team.
You care about impact, not noise: You care deeply about the substance of your work. You measure success by results, not recognition and you let your work speak for itself.
You’re energized by complexity and ambiguity: You enjoy tackling problems that don’t come with a playbook. You’re comfortable building from scratch, iterating as you go, and collaborating to shape the best path forward.
You seek out feedback: We value directness, clarity, and respect. We believe honesty fuels great work and career growth. You see feedback as a tool for learning and improvement, and you know that open, honest dialogue is key to achieving the best results — together.
You’re here for more than a job: At Relay, everything we do is in service of our mission to help small businesses thrive. To drive impact and have purpose here, that mission must matter to you too.
Our Promise
We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take chances, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.
What’s Important to Us:
Research shows that women-identifying and other marginalized individuals often apply only if they meet 100% of the qualifications. But no one is a perfect match on paper. If this role excites you, we’d love to hear from you and figure out together if it’s a great fit.
At Relay, we believe that diversity is key to building high-performing teams, and creating an inclusive work environment is our priority. We are an equal opportunity employer and welcome people of diverse backgrounds, perspectives, and skills.
We will work with applicants to provide accommodations at any stage of the hiring process. If you require accommodations during the interview process, please email your Talent Partner, and we will work with you to meet your needs.
