Director, Sales Solutions Engineering

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? About the Role This role is the tip of the spear for Flex's largest, most complex, and most strategically important deals. As we expand into new verticals and new enterprise relationships, we need a technical sales leader who can do more than present a demo. You'll own the solution layer of the sales process end-to-end: translating complex customer environments into winning proposals, building conviction with technical and executive stakeholders alike, ensuring that what we promise is something we can actually deliver, and working with Product & Engineering teams to ensure customer needs are a key input to internal roadmaps. This is the founding hire for Flex's New Verticals Solution Engineering function. You'll start as a hands-on, high-impact operator with Director-level scope, and you'll build the foundation the function scales on: the playbooks, the demo environments, the discovery frameworks, and the hiring plan. As new vertical pipeline matures, you will recruit, hire, and lead a team of Solution Engineers, with a defined path to formal people leadership of the SE organization. We are looking for someone who wants to earn that mandate by winning deals first, then scale themselves through a team. What You'll Do • Own the technical sale on our largest, most complex deals: Lead solution engineering activity for Flex's highest-priority opportunities in new verticals, from discovery and scoping through proof-of-concept, technical validation, and close. • Build trust with technical and executive buyers: Engage executive stakeholders at prospective partners. Translate Flex's capabilities into business outcomes that resonate at the board level and in the weeds equally. • Architect solutions that win and scale: Deeply understand each prospect's technology, data environment, and operational requirements. Design integration and deployment approaches that are commercially compelling and technically sound, working shoulder-to-shoulder with Flex Engineering to validate feasibility before we commit. • Drive proof-of-concept and pilot execution: Lead structured POCs and pilots that de-risk the decision for the customer and accelerate time-to-close. Define success criteria, coordinate Product and Engineering resources, manage execution, and turn results into momentum. • Partner with Sales to shape deal strategy: Function as a true co-owner of the deal alongside the Account Executive, contributing to account strategy, surfacing risks, and helping design the right commercial and technical structure. • Build the New Verticals SE function, not just the playbook: Document discovery frameworks, integration patterns, objection handling, and competitive differentiation as we enter each new vertical. Create reusable assets (demo environments, solution briefs, RFP libraries) that raise the floor for future deals and make every SE hire behind you productive faster. • Define and execute the SE hiring plan: Build the business case for headcount as vertical pipeline scales. Own the hiring bar: write role profiles, design the interview process, recruit, and onboard the first Solution Engineers on the team. • Grow into leading the team: As the function scales, transition from founding IC to player-coach to people leader. Set the operating rhythm, coach SEs on deal execution, and own quality across the SE motion in new verticals. • Partner deeply with Product and Engineering: Operate as the connective tissue between the field and the build. Synthesize technical feedback from deals into structured, prioritized product input, align Engineering on customer requirements during active cycles, and influence the roadmap by making the business case for what new verticals require. • Shape how Flex shows up in market: Partner with Marketing and Business Development on technical content, event presence, and thought leadership that builds Flex's credibility with enterprise buyers in new segments. Key Qualifications • 10+ years of experience in pre-sales, solutions engineering, or technical sales, with at least 4 years operating in a senior or lead capacity on complex enterprise deals. • Demonstrated track record closing large, multi-stakeholder, technically complex sales cycles, ideally in FinTech, PropTech, payments, or adjacent SaaS/infrastructure categories. • Experience building or scaling an SE or technical pre-sales function: hiring SEs, developing talent, and establishing the processes and assets a team runs on. Formal people management experience is a strong plus; demonstrated readiness and ambition to lead a team is required. • Exceptional ability to engage and build credibility with C-suite and VP-level technical buyers; equally comfortable in a boardroom and in a technical architecture review. • Deep fluency in enterprise integration patterns (APIs, webhooks, data pipelines, ERP/property management system ecosystems) with the ability to get hands-on when needed. • Strong commercial instincts: ability to shape deal structure, anticipate objections, and understand how technical decisions affect economics on both sides of the table. • Experience operating in a greenfield or early-stage vertical context. Comfortable building process, playbooks, and teams from scratch rather than inheriting them. • Track record of functioning as a cross-functional bridge: influencing product roadmaps, aligning engineering teams to customer requirements, and partnering closely with marketing and BD. • Outstanding written and verbal communication; the ability to distill complex technical and financial concepts into clear, persuasive narratives for diverse audiences. • High ownership orientation: someone who treats the customer's success as their own, moves urgently without needing to be told to, and multiplies their impact through the people they hire and develop. • FinTech, real estate technology, or multi-sided marketplace experience is a strong plus. Compensation The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. This is a commission earning role. The OTE (On Target Earnings) listed below: OTE (NYC/Bay Area, Los Angeles, Seattle) $230,000—$290,000 USD OTE (Salt Lake City, all other USA cities) $195,000—$245,000 USD Life at Flex We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace. Offices Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program. Benefits For full-time U.S. employees we offer: • Competitive medical, dental, and vision • Company equity • 401(k) plan with company match • Unlimited paid time off + 13 company paid holidays • Parental leave • Free Flex subscription For full-time non-U.S. employees, we offer: • Competitive compensation + company equity • Unlimited PTO