Director, Customer Onboarding

Relay is a digital banking platform that gives self-made business owners the tools and know-how to be great with money—bringing clarity, confidence, and control to every dollar earned, so they can turn hard work into lasting success. We do this by replacing financial guesswork with real visibility, transforming cash flow from a constant source of stress into a clear signal owners can use to run stronger, more resilient businesses.

At Relay, onboarding is where customer trust turns into habit, product value, and durable revenue. Our Director, Customer Onboarding will own the strategy, operating model, and performance of our onboarding function across acquisition sources, including Direct, Product-led, and Advisor Partnerships referral-led customers. The Advisor channel is a meaningful growth driver for Relay and includes onboarding SMBs referred by accounting and bookkeeping partners.

This role will lead the team responsible for driving product activation and early revenue outcomes for customers receiving human-led onboarding in our higher value segments, while building scalable, lower-touch programs for customers who primarily self-onboard. You will be accountable for how effectively customers move from sign-up to meaningful usage milestones and how the onboarding function partners with Sales, Advisor Partnerships, Product, Support, Growth, and RevOps to remove friction and scale a best-in-class experience.

If you thrive in ambiguity, know how to use data to shape strategy, and love building systems that scale through both people and product, this role is for you.

What You’ll Be Doing

Onboarding Strategy and Segmentation

• Own the multi-year vision and near-term strategy for Customer Onboarding.

• Build a tiered and segmented onboarding motion across revenue bands and acquisition sources.

• Define what great activation looks like for each segment and channel, aligning onboarding milestones to long-term usage, retention, and revenue outcomes.

• Establish a clear framework for when human-led onboarding is the right investment versus scaled and product-led interventions.

• Ensure the onboarding strategy supports both customer outcomes and efficient cost-to-serve.

Team Leadership and Development

• Lead and develop a high-performing team of onboarding specialists.

• Build a coaching culture with clear performance expectations, role clarity, and growth pathways.

• Drive organizational design and capacity planning to ensure the team can scale with growth.

• Partner with Talent and Enablement to refine hiring profiles, ramp plans, and ongoing training.

Operational Excellence

• Own end-to-end onboarding workflows, playbooks, and documentation to improve speed, consistency, and scalability.

• Establish a rigorous operating cadence that includes weekly performance reviews, cohort health reviews, QA, and quarterly planning.

• Identify bottlenecks in the onboarding journey and drive improvements across people, process, and product.

• Define and maintain service levels and internal handoff standards across Sales, Advisor Partnerships, Support, and Onboarding.

Data and Performance Rigor

• Partner with RevOps and Data to build dashboards and cohort views that track onboarding performance at 30, 60, and 90-day horizons.

• Diagnose performance differences between human-touched and self-serve cohorts and translate insights into clear prioritization and investment cases.

• Design and run experiments to measure incremental impact of onboarding plays and scaled programs.

• Own quarterly and annual target setting for onboarding outcomes tied to activation and early revenue.

Scaled Onboarding and Lifecycle Programs

• Build and ship scalable onboarding experiences including webinars, guided setups, in-product journeys, and lifecycle campaigns.

• Pilot and implement automation and AI-driven tools to extend high-quality onboarding into lower-touch segments.

• Create trigger-based intervention programs for accounts at risk of stalling early in their journey.

Cross-Functional Leadership

• Partner closely with Direct Sales, Advisor Partnerships, Product, Marketing, Support, and Growth to create clean handoffs and consistent customer journeys.

• Build a referral-specific onboarding and activation path for partner-sourced SMBs that improves time to value and early revenue outcomes.

• Represent onboarding strategy and results in leadership forums.

• Provide structured feedback to Product on onboarding friction, activation blockers, and feature adoption gaps.

Who You Are

• 8+ years of experience in onboarding, implementation, customer success, lifecycle growth, or adjacent roles within SaaS or fintech.

• Strong operational builder who can create repeatable systems, playbooks, and cadences that improve performance over time.

• Highly data-driven, comfortable using cohort analysis, funnel metrics, and experimentation to inform decisions and prove impact.

• Cross-functional leader with strong influence and a track record of shaping product and lifecycle priorities to remove onboarding friction.

• Deep customer empathy paired with urgency and accountability.

• Comfortable balancing strategic planning with hands-on execution in a fast-growing environment.

Bonus Points

• Experience in SMB fintech, banking, accounting software, or vertical SaaS.

• Experience designing multi-source onboarding motions that include referral-led acquisition.

• Experience building activation frameworks tied directly to revenue and retention.

• Experience partnering closely with Product teams to evolve in-product onboarding.

What Success Looks Like

• Activation lift in team-supported segments: A measurable improvement in activation milestones and early revenue performance for higher value cohorts receiving human-led onboarding.

• Reduced time to value: More customers reaching first meaningful milestones within target timeframes.

• Scaled lower-tier motion: A cost-effective, data-backed program that improves outcomes for self-onboard cohorts using trigger-based and digital interventions.

• Advisor referral activation: Clear playbooks and measurable activation improvement for partner-referred SMBs, with a strong feedback loop to Advisor Partnerships.

• Operational maturity: Documented, scalable processes and a predictable performance cadence with clear accountability.

• Team growth: Strong talent development, retention, and consistent performance against expected standards.

• Cross-functional impact: Meaningful onboarding improvements shipped through product and lifecycle changes informed by onboarding insights.

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 three days 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.

The Interview Process

• Stage 1: A 30-minute Google Meet video call with a member of the Talent team

• Stage 2: A 45-minute Google Meet video call with our Head of Sales

• Stage 3: A 45-minute in-person interview with a member of the Leadership team

• Stage 4: A 45-minute in-person interview with our CEO

• Stage 5: Two-part case study

• Part 1: 45-minute live whiteboard discovery session

• Part 2: 60-minute presentation of your proposed strategy for the Customer Onboarding function

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.

Disclaimer: For compliance reasons, all offers of employment at Relay are conditional upon a successful background check & employment verification through Certn.