Go-To-Market Engineer, Flex
$136-170k
+ Equity
2-3 days a week in office
Flexible rent payment application
Open for applications
Flexible rent payment application
501-1000 employees
Open for applications
$136-170k
+ Equity
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
- 5+ years of experience in Revenue Operations, Sales Operations, or GTM Systems in a high-growth SaaS or FinTech environment, with a trajectory into technical or AI-focused work
- Hands-on experience deploying and iterating AI-powered workflows, automations, or agents in a live B2B revenue environment — shipping and maintaining production systems, not just scoping or advising
- Deep working knowledge of the revenue tech stack, including Salesforce, Clay, Snowflake, Outreach, or equivalent platforms — with strong command of how data moves between them
- Proficiency with Claude Code and/or Codex for workflow automation, prompt design, and agentic task orchestration, including the ability to build, version, and maintain shareable skills and plugins
- Hands-on experience configuring MCP (Model Context Protocol) infrastructure and integrating AI agent frameworks into live GTM workflows
- Strong command of APIs, system integrations, and connected app architecture — you understand where data breaks across platforms and how to design integrations that hold at scale
- Demonstrated expertise in data governance principles — you've built or enforced practices that keep revenue data clean, trustworthy, and AI-ready
- Strong cross-functional communication skills, with the ability to translate technical systems and outcomes for non-technical stakeholders from ICs to C-suite
What the job involves
- Operating at the intersection of RevOps and AI engineering, you will embed with Go-To-Market (GTM) teams to design and ship the automation and agent infrastructure that drives leverage. Rather than advising, you will build and iterate in production to scale Flex's revenue motion
- Success involves replacing manual tasks with high-judgment work that closes deals and retains customers. As a builder and cross-functional partner, you will collaborate with Sales, RevOps, and the central AI team to ensure AI adoption delivers measurable business results
- Co-owns revenue team's AI initiative roadmap — planning, prioritizing, and measuring the success of AI programs against pipeline generation, efficiency, and retention outcomes
- Design and deploy AI-powered workflows, automation agents, and outbound prospecting systems that reduce manual lift for Sales, BDR, and Partner Success teams
- Configure and manage MCP infrastructure and AI agent tooling across the GTM org, ensuring systems are discoverable, actively adopted, and continuously improving
- Integrate and maintain Flex's GTM tech stack — Salesforce, Clay, Snowflake, Outreach, and adjacent platforms — so data flows between systems without manual intervention
- Enforce data governance standards across revenue systems, ensuring AI models and agents are built on clean, trustworthy, well-documented data foundations
- Build and maintain a shared library of AI skills, prompts, and agent context (including Claude Code–built skills and plugins) that the broader revenue team can access and reuse
- Partner with Enablement to champion AI adoption across the revenue org — translating technical work into business outcomes, tracking adoption, and representing GTM use cases to Flex's central AI function
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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