Director of Sales Solutions Engineering

Flex; San Francisco (CA); On-site; USD 180,000 - 290,000; Full time

Benefits offered by this job

Healthcare benefits

Parental Leave

Hybrid work

401(k) match

Flex Giving

Employee assistance

Unlimited PTO

GrubHub credits

Free Flex subscription

NYC HQ

Job summary

Flex seeks a technical sales leader to spearhead its New Verticals Solution Engineering function in San Francisco. You will own end-to-end solution design, translate customer environments into winning proposals, and build conviction with executive stakeholders while aligning with Product & Engineering to feed the roadmap.

As the founding SE leader, you’ll create playbooks, demo environments, discovery frameworks, and an initial hiring plan, with a path to scale into a team and leadership of the

Qualifications

• Demonstrated track record closing large, multi-stakeholder, technically complex sales cycles.
• Experience building or scaling an SE/technical pre-sales function including hiring and processes.
• Formal people management experience is a strong plus; readiness to lead a team.
• Experience in FinTech, PropTech, payments, or adjacent SaaS/infrastructure is a plus.
• Experience operating in greenfield or early-stage vertical contexts; building processes from scratch.
• Outstanding ability to engage with C-suite and VP-level buyers; boardroom and architecture reviews.
• Track record as cross-functional bridge guiding product, engineering, marketing and BD.
• High ownership orientation; focus on customer success and scalable impact through hiring.

Responsibilities

• Own the technical sale on our largest, most complex deals from discovery through proof-of-concept, technical validation, and close.
• Lead solution engineering activity and build conviction with technical and executive stakeholders.
• Architect solutions that are technically sound and commercially compelling; validate feasibility with Engineering.
• Drive POCs and pilots; define success criteria and coordinate Product/Engineering resources.
• Partner with Sales to shape deal strategy; co-own the deal with Account Executive.
• Build the New Verticals SE function: create playbooks, demo environments, discovery frameworks, and hiring plan.
• Define and execute the SE hiring plan; recruit and onboard first Solution Engineers.
• Grow into people leadership; set operating rhythm and coach SEs.
• Collaborate with Product and Engineering; translate feedback into roadmap input; influence roadmap for new verticals.
• Shape market presence with Marketing/BD through technical content and events.

Skills

Enterprise sales

Solution engineering leadership

Pre-sales

Cross-functional collaboration

Executive stakeholder engagement

Deal structuring

Sales process optimization

C-suite credibility

Job description

• 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
• 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

Benefits

• Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
• Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
• NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
• 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
• Flex Giving: Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
• Employee Assistance Fund: Confidential financial support to teammates facing unexpected hardships or emergencies.
• Hybrid Work Policy: Work flexibly from home, with in‑person collaboration and events that matter.
• Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
• Free Flex Subscription: As a Flex employee, you’ll have full access to our services without charge.
• GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead.

Requirements

Demonstrated track record closing large, multi-stakeholder, technically complex sales cycles, ideally in FinTech, PropTech, payments, or adjacent SaaS/infrastructure categoriesExperience 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 requiredFinTech, real estate technology, or multi‑sided marketplace experience is a strong plusExperience operating in a greenfield or early‑stage vertical context. Comfortable building process, playbooks, and teams from scratch rather than inheriting themExceptional ability to engage and build credibility with C‑suite and VP‑level technical buyers; equally comfortable in a boardroom and in a technical architecture reviewHigh 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 developTrack record of functioning as a cross‑functional bridge: influencing product roadmaps, aligning engineering teams to customer requirements, and partnering closely with marketing and BD10+ 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 dealsDeep fluency in enterprise integration patterns (APIs, webhooks, data pipelines, ERP/property management system ecosystems) with the ability to get hands‑on when neededStrong commercial instincts: ability to shape deal structure, anticipate objections, and understand how technical decisions affect economics on both sides of the tableOutstanding written and verbal communication; the ability to distill complex technical and financial concepts into clear, persuasive narratives for diverse audiences