Location: Remote (US), Bay Area preferred

Reports to: CEO

About Fleak

Fleak is the AI-native ingestion and translation layer for enterprise security and observability data. Our engine parses, normalizes, and routes logs and telemetry into a customer's target schema (OCSF, vendor CIMs, homegrown models) at runtime, with AI-generated parsers and confidence scoring instead of hand-built pipelines. We sit behind top-tier security and observability platforms as the layer that turns messy source data into schema-ready data — including agent-to-agent workflows where AI agents call our MCP server to prepare OCSF-ready data with no human in the loop. 

We are founder-led on sales today (CEO and CTO are the only sellers). We have production references at top-tier security/observability platforms, a quantified token-economics ROI (~40% lower agent token cost at same model and accuracy, from a joint benchmark), a packaged MSP/channel motion, and a strategic path with a large ecosystem partner who is also an investor. We are hiring a VP of Sales to convert those assets into a repeatable revenue engine.

The role

You will own revenue as our first dedicated sales leader. This is a founding, hands-on role for someone who loves being in the room and closing: you take the founder-led motion, make it your own, and turn it into a repeatable engine by selling it. You will inherit live motions — strategic partner co-sell, CISO dinners, an MSP/MSSP channel, and a targeted outbound program — plus production references and a quantified ROI story to sell with. Your job is to convert those assets into signed, expanding customers.

This is the ground floor. You will define how Fleak sells, close the deals that prove the model, and shape the organization that grows out of your success. It's the right seat for an operator who thrives at seed stage and wants outsized ownership and equity for the revenue they build.

What you'll do

• Own and personally close the net-new ACV number. Source, qualify, and drive deals to signature, and bring pipeline discipline, stage definitions, and reply-to-meeting-to-opportunity tracking to a motion that already sees strong response rates.

• Take the founder-led motion and codify it into a repeatable playbook by running it, freeing the founders from being in every room.

• Own the channel and strategic-partner motion end to end. Recruit and activate MSP/MSSP partners around a low-friction land SKU, and drive the co-sell path with our strategic ecosystem partner from POC to first joint account.

• Turn our production references and token-economics ROI into closed pipeline: CISO dinners, warm and precise outbound, and event/community sourcing.

• Sharpen pricing and packaging with the CEO into a clean land-and-expand story.

• Instrument the funnel and report on it clearly: what's qualified, in what stage, closing when.

What we're looking for

• 10+ years in enterprise software sales, with significant time at an early-stage or high-growth startup; you have personally carried and beaten a quota and closed complex deals yourself.

• Domain fluency in the infrastructure, data pipeline, security, or observability space. You can hold a technical conversation with a security engineer about schema normalization, OCSF, SIEM/XDR data onboarding, and agent workflows, and a commercial conversation with a CISO about token economics and ROI.

• A live, relevant rolodex — enterprise security/observability buyers and channel/OEM partners you can call this quarter. Experience selling both direct enterprise and through MSP/MSSP/OEM channels.

• Command of complex, multi-stakeholder deals: six-figure-plus ACV, ELA/OEM structures, POC-to-production motions, and co-sell with a large platform partner.

• A founder's mentality: you set strategy and forecast, and you love being in the room closing. You are energized by building something from the ground up and owning the outcome.

• You thrive in the ambiguity of early-stage startups — comfortable with imperfect data, self-directed, and quick to build the structure you need rather than wait for it.

Nice to have

• Direct experience at a data-infrastructure, security-data-pipeline, or observability company that scaled through a partner/ecosystem motion (e.g., data streaming/pipeline, SIEM/XDR, or telemetry vendors).

• Existing relationships in the OCSF community, the MSSP/MDR ecosystem, or with major SIEM/observability platform teams.

• Track record turning a design-partner or reference customer into a repeatable, named case study and co-sell relationship.

Why this role

Fleak has message-market fit where targeting is right (40–90% reply rates on precise segments), production references at names that matter, a hard-dollar ROI story, and a strategic partner on the cap table. You get to build the revenue engine on top of it — with a direct line to the CEO, real ownership, and meaningful equity. As you prove the motion, the organization grows around you.