Director of Sales Solutions Engineering, Flex
$232-290k
+ Equity
More information about location
2-3 days a week in office
Flexible rent payment application
Posted today
Flexible rent payment application
501-1000 employees
Posted today
$232-290k
+ Equity
More information about location
2-3 days a week in office
501-1000 employees
Company mission
To help people pay for the things that matter most.
Role
Who you are
- 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
What the job involves
- 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
Our take
Many people struggle to pay their rent every month, with a variety of bills hitting their bank accounts simultaneously. Whilst many of these people earn enough money to cover their bills, the inflexible nature of monthly bills can make the all-in-one payment a harder obstacle.
Flex provides a mobile application for the flexible payment of rent, allowing users to pay their landlords through flexible payment plans, reschedule payments when necessary, and protect their funds through Overdraft Protection. The company achieves this by partnering with estate agents and paying their resident's bills upfront, taking on the challenges that landlords would normally have due to late payments.
Flex has experienced extremely rapid growth since its founding which has caused some issues, as it struggled to keep up with the surge in new customers. Having made improvements to its product and scaled its customer service team, it is set to continue providing a service that has come to be highly valued by both tenants and landlords.
Freddie
Company Specialist at Welcome to the Jungle
Insights
10% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2022
$160m
SERIES C
Apr 2021
$46.6m
SERIES B
Total funding: $225.1m
Company 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.
Company HQ
Midtown Manhattan, New York, NY
Leadership
Shragie Lichtenstein
(Co-Founder & CEO)Prior to co-founding Flex in 2019, Shragie co-founded Boundless Reality. They graduated from Yeshiva University in 2015 with a Bachelor's Degree in Finance.
YeTong Shao
(Co-Founder)Prior to co-founding Flex in 2019, YeTong co-founded Boundless Reality alongside Shragie. They graduated from the University of Chicago with a Bachelor's Degree in Mathematic & Economics.
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