Affirm · Toronto
Sales & BusinessRemoteposted 2mo ago
Affirm is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest.
The Revenue team drives Affirm’s top-line growth through strategic partnerships, pricing, and go-to-market execution. We acquire, retain, and expand merchant relationships across eCommerce, in-store, telesales, and the Affirm app. The team leads onboarding, relationship management, and performance optimization to help partners succeed. We deliver value-added solutions, drive adoption, and support long-term business growth by connecting merchants and consumers through Affirm’s products.
We’re looking for a Sr. Manager, Key & Enterprise Sales (US + CA) to lead a portfolio of strategic opportunities across Travel and New Markets in the US and all Key accounts in Canada. Reporting to Director & Head of Key & Enterprise Sales for Travel, New Markets, and International, this leader will oversee 6 experienced Account Executives and work with some of Affirm’s most strategic merchants across airlines, OTAs, hotels, car rental, cruises, healthcare and the largest Canadian accounts across all verticals.
This leader will execute and evolve the go-to-market plans in partnership with senior leadership, build executive relationships, guide complex commercial opportunities, and turn strategy into measurable business results. They will lead a high-impact team and partner across the business to help Affirm win, launch, and grow strategic merchant relationships.
Lead and mentor a team of mid-to-senior-level Key and Enterprise Account Executives, helping them develop strategies to win new business and expand existing partnerships.
Own executive stakeholder management for the segment: communicate progress and risks early, align on tradeoffs, and support senior leadership decision-making; lead executive-level negotiations with strategic partners.
Execute and continuously refine the US Travel & New Markets and Key CA GTM plans and operating rhythm (segmentation, coverage, merchant prioritization, pipeline inspection), partnering with Sales Ops/RevOps to improve forecasting accuracy, operational effectiveness, and team performance.
Lead cross-functional deal orchestration for priority opportunities, building alignment across Legal, Product, Risk, and Client Success to navigate complex deal requirements and drive successful outcomes.
Navigate complex and ambiguous commercial situations, balancing merchant needs, business objectives, operational constraints, and risk considerations to make informed decisions.
Recruitment & Team Development: Support hiring, onboarding, and calibration for the team in partnership with sales leadership and People, ensuring swift decision-making and momentum.
Drive team execution across deals, providing hands-on coaching from pipeline development through negotiation and close; leverage AI-enabled call/notes synthesis and deal-cycle organization (e.g., mutual action plans, risk capture, next steps) to remove blockers and maintain a high bar for deal quality.
Partner with Client Success, Product, and Technical Account Management to ensure a smooth launch and strong early performance for newly signed merchants; proactively manage escalations and post-close handoffs.
Identify and drive first-year expansion opportunities (cross-channel, multi-brand, or new use cases) for Travel and New Markets partners, in alignment with leadership priorities.
Bring structure and innovation to sales execution and pipeline management, including standardization of deal artifacts and operating cadences, improving efficiency and consistency across the team.
Hold the team accountable for performance, providing timely coaching, feedback, and development while creating clarity around priorities, execution expectations, and business outcomes.
Represent Affirm at industry events and conferences relevant to Travel and priority new markets, strengthening our position in the market.
Travel regularly to lead executive engagements, accelerate deal cycles, and facilitate team planning sessions and off-sites.
10+ years of solution selling experience, including 3+ years of leadership experience managing high-performing sales teams.
A strategic and hands-on sales leader with a deep understanding of enterprise sales and complex deal structures.
Experience translating strategy into operational plans and team execution, driving sustained results through forecasting rigor, pipeline inspection, and strong cross-functional collaboration.
Demonstrated ability to drive cross-functional execution across Product/Legal/Risk/CS for complex enterprise partnerships.
Demonstrated operational excellence in forecasting, pipeline management, and sales execution.
Demonstrated ability to navigate ambiguity, solve complex business problems, and make sound decisions with incomplete information.
Proven track record of selling into large, enterprise merchants; Travel experience strongly preferred (and/or experience incubating new verticals/markets).
Strong alignment with Affirm’s mission, with a passion for building financial products that improve lives.
Strong executive presence and ability to build relationships with senior stakeholders internally and at major brands.
An active networker who can broker warm leads and open doors to new opportunities.
A structured, organized leader who brings new ways of thinking and managing to the team.
A proactive, entrepreneurial mindset with the ability to navigate ambiguity and drive initiatives forward.
A strong coach and mentor who holds the team accountable and provides real-time, constructive feedback to improve performance.
Willingness to travel regularly to support deal acceleration, industry events, and team collaboration.
Pay Grade - M
Equity Grade - 10
Employees new to Affirm typically come in at the start of the pay range. Affirm focuses on providing a simple and transparent pay structure which is based on a variety of factors, including location, experience and job-related skills. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, which includes the annual base pay and the sales incentive target.
Base pay is part of a total compensation package that may include equity rewards, monthly stipends for health, wellness and tech spending, and benefits (including 100% subsidized medical coverage, dental and vision for you and your dependents.)
USA On Target Earnings (CA, WA, NY, NJ, CT) per year: $370,000 - $490,000
USA On Target Earnings (all other U.S. states) per year: $328,000 - $448,000
Please note that visa sponsorship is not available for this position.
#LI-Remote
Affirm is proud to be a remote-first company! The majority of our roles are remote and you can work almost anywhere within the country of employment. Affirmers in proximal roles have the flexibility to work remotely, but will occasionally be required to work out of their assigned Affirm office. A limited number of roles remain office-based due to the nature of their job responsibilities.
We’re extremely proud to offer competitive benefits that are anchored to our core value of people come first. Some key highlights of our benefits package include:
We believe It’s On Us to provide an inclusive interview experience for all, including people with disabilities. We are happy to provide reasonable accommodations to candidates in need of individualized support during the hiring process.
[For U.S. positions that could be performed in Los Angeles or San Francisco] Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles Fair Chance Initiative for Hiring Ordinance, Affirm will consider for employment qualified applicants with arrest and conviction records.
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