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Flex is building the AI-native private bank for business owners.
We’re re-architecting the entire financial system for entrepreneurs—from the first dollar a business earns to how that value compounds, moves, and is ultimately spent in real life. Banking, credit, payments, personal finance, and financial operations—rebuilt from the ground up as a single, intelligent system. Flex is the full financial home for ambitious owners.
Since launching publicly in September 2023, Flex has scaled from zero to nine-figure annualized revenue, with a clear path to profitability by late 2026. We move fast, ship relentlessly, and operate with extreme ownership.
Our customers are affluent business owners ($3–$200M in revenue)—the backbone of the economy and one of the most underserved segments in finance. They’re stuck with outdated banks and fragmented tools. We’re replacing all of it. The opportunity is massive: a ~$1T+ revenue market hiding in plain sight. Our ambition is to build a $100B+ company by delivering a product that is fundamentally better—not incrementally improved.
Flex has raised $100M+ in equity and $300M+ in debt.
- Mission-critical problems: We build software that directly controls how money moves at scale.
- High bar, low ego: Small teams, exceptional people, real ownership.
- Speed over comfort: We prioritize execution, quality, clarity, and results.
- Enduring impact: What we’re building will define how a generation of owners runs their businesses.
We hire exceptional people who want to build hard things and see their work matter immediately. Roles are available in: San Francisco, Miami, New York, and fully remote.
Flex Fuels Ambition.
This is Flex's first dedicated Sales Enablement hire — and it's not a maintenance role. There's no inherited playbook to manage, no existing LMS to administer, no certification path waiting to be run. You're building from scratch, and that's the point.
As Manager, Sales Enablement, you'll be the force multiplier across a GTM team of ~30 people today — AEs, BDRs, and a partnerships team — that is growing rapidly. The programs you build now need to work at 2x and 3x this size, and you'll be shaping this function as that growth happens. You'll report to the Director of Revenue Operations and work closely with sales leadership, product marketing, and the broader RevOps function to design, build, and measure programs that have a direct line to revenue.
AI is not a nice-to-have here. You're expected to leverage AI tools to build smarter content, run more efficient programs, and multiply your own output as the sole enablement practitioner. The candidate we're looking for sees a lean org as an advantage, not a constraint.
Your work will have direct reach beyond the GTM team — helping product and engineering stay grounded in how customers actually buy and what reps encounter in the field. At Flex's current scale, the feedback loop between GTM and R&D is a competitive advantage, and this role is part of how we close it.
If you're energized by building something from zero, measuring everything, and being directly accountable for whether reps succeed — this role was built for you.
Design and own end-to-end onboarding programs for AE, BDR, and partnerships roles — covering product knowledge, sales process, tool proficiency, and Flex's ICP
Build role-specific certification paths and 30/60/90-day ramp benchmarks; track and report on time-to-productivity for every new hire
Partner with sales managers to identify where new reps are breaking down and close those gaps fast
Develop and maintain a living sales playbook by segment — covering AE, BDR, and partner motions — updated quarterly or as the product and market evolve
Build and manage a content library: battle cards, objection-handling guides, competitive positioning, case studies, and discovery frameworks
Own call coaching infrastructure via Apollo — build review cadences, scorecards, and feedback loops that make managers more effective coaches
Facilitate enablement sessions (live, async, and AI-assisted) that are role-specific and tied to real deal scenarios, not generic training content
Champion and reinforce a consistent sales methodology across AE and BDR teams — including discovery, qualification, and multi-stakeholder navigation
Partner with RevOps to ensure Salesforce stages, fields, and dashboards reflect how the team actually sells
Identify execution gaps in the funnel (conversion rate drops, stage stall, ACV variance) and build targeted programs to address them
Own the sales enablement workstream for every new product launch — from pre-launch rep readiness and certification to post-launch reinforcement and feedback loops back to product; at Flex's current pace of product development this is a core, recurring responsibility not a one-off project
Partner with the RevOps Director on sequence strategy and outbound tooling (Clay, Apollo, Orum) to ensure BDR enablement keeps pace with GTM experiments
Define and own a core set of enablement KPIs: ramp time, content adoption, methodology adherence, win rate by segment, and pipeline conversion by rep cohort
Report on program effectiveness to sales leadership on a regular cadence and use that data to continuously improve
4–6 years in sales enablement, revenue enablement, or a closely related role at a B2B company — ideally with some fintech or financial services experience
Proven track record of building enablement programs from scratch in a high-growth, resource-constrained environment
Salesforce proficiency — comfortable building reports, understanding stage hygiene, and partnering with admins on configuration needs; familiarity with Apollo and ZoomInfo as part of the GTM stack is a plus
Hands-on experience with an LMS or knowledge management platform; able to design and deliver multi-modal learning (async, live, self-paced)
Fluency with AI tools (Claude, ChatGPT, or equivalent) as a real part of your workflow — content creation, program design, and output acceleration
Experience building structured qualification and discovery frameworks into a sales process — whether homegrown or methodology-based — and the ability to get a team to actually use them
Strong written and verbal communication skills; able to produce crisp executive-facing materials and also sit in a deal debrief and translate what you heard into program improvements
High ownership instinct — you identify gaps without being asked and move on them without waiting for consensus
Experience supporting both an outbound BDR motion and a consultative AE motion simultaneously
Familiarity with Clay, Apollo, or Orum in the context of BDR enablement
Experience with a partner or channel enablement motion
Prior experience at a company that went through rapid AE headcount scaling (2x–4x in a 12–18 month window)
SQL or BI tool comfort (Hex, Looker, or similar) — ability to pull your own data rather than depend on analysts
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Flex is a financial technology platform that lets renters split their monthly rent into two installments aligned with their paycheck schedules. The company serves over 2 million renters and has facilitated more than $20 billion in rent payments. Membership is $14.99/month plus 1% of rent, and on-time payments are reported to credit bureaus at no additional cost.
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