Founding Enterprise Account Executive - Tech

Sierra Ventures; Palo Alto (CA); Hybrid; USD 150,000 - 210,000; Full time

Job summary

Sierra Ventures is seeking a hands-on, builder-seller who thrives in a founder-led motion. You will own deals end-to-end, from discovery to close, while learning and expanding our enterprise sales playbook.

This role emphasizes rapid learning, high tempo, and the ability to navigate security, legal, and procurement with founder support. You will build your own book, source and expand customers, and work across engineering and product to translate customer problems into concrete business value.

Qualifications

• 4+ to 12+ years of professional experience in B2B sales, including enterprise accounts.
• Experience selling AI, data, infrastructure, or developer-tools to engineering/data leaders is a plus.
• Strong outbound, events, and follow-through are essential.

Responsibilities

• Work with founders on high-profile enterprise accounts from discovery to close.
• Learn and scale the founder-led playbook, then lead and improve it.
• Build target account lists and buyer maps; run outbound and follow-up with AI-assisted research.

Skills

B2B sales

Enterprise selling

Outbound and events

Product fluency

Ownership and communication

Mindset

Education

Bachelor's degree or equivalent experience

Tools

Apollo

Lightfield

Devin

Lovable

Job description

Who are we

We're a tight-knit, collaborative team on a mission to make knowledge accessible to everyone in an organization - building the durable layer where decisions, context, and institutional know-how live so no one is left hunting through Slack or piecing together what happened.

If you love working where curiosity is contagious, ideas travel fast, and the work you ship tangibly changes how teams think and build, you'll fit right in.

In this role, you will

• Work alongside the founders on high-profile enterprise accounts, from discovery to close

• Learn the founder-led playbook (already working and producing revenue), then run it and improve it

• Build target-account lists and buyer maps (engineering, data, and AI leaders), and run outbound and follow-up, using AI tools to research and personalize faster

• Choose the right conferences and events, then prepare, start conversations, and follow up fast

• Run discovery and live technical demos, and turn messy customer problems into a clear business case and next step

• Work through security reviews, legal, and procurement with founder support

• Know when to bring in founders, product, or engineering, and stay the quarterback on your deals

• Build your own book: source, open, close, and expand customers you own

• Feed customer learning into ICP, messaging, demos, and product

• Keep CRM, follow-up, and the forecast clean and current, with AI doing the busywork

We're looking for an hands-on builder-seller who is hungry, resourceful, and quick to learn, with a record of owning deals. You keep a high operating tempo, you are comfortable doing the unglamorous work, and you want to take over more and more of a working founder-led motion. This is a hands-on individual contributor role, not a management role.

This is a chance to learn enterprise selling at close range with the founders and help land important customers. You start alongside them, take on more of the cycle as you ramp, then apply the same proven playbook to build a customer base of your own.

You may be a good fit if you

• Education: Bachelor's degree in a related field, or equivalent practical experience.

• Experience: 4-12+ years of professional experience in B2B sales, including time carrying a number at a software, AI, or developer-tools company. Strong early-career and seasoned enterprise sellers are both welcome.

• Sales skills: You have sourced, advanced, and closed real deals. Time selling AI, data, infrastructure, security, or other technical products to engineering and data leaders is a plus.

• Outbound and events: You start from a blank list: research, messages, calls, events, follow-through.

• Product fluency: You learn an AI-native product fast, can explain how LLMs, agents, and context infrastructure work in plain words, run a solid technical first conversation, and know when to bring in engineers.

• Ownership and communication: You are self-directed, write clearly, and keep accountability after a handoff.

• Mindset: You value hunger, learning speed, and ownership over title, and you value different perspectives.

Our motion

• Channels: Targeted outbound Events Referrals Selected ecosystem partners

• Sales path: Discovery Tailored demo Scoped evaluation or pilot Production Expansion

• Working model: Own your pipeline Involve the founders and team deliberately Never drop accountability at a handoff

• Tools: Apollo (prospecting) Lightfield (CRM) Devin and Lovable (demos) AI assistants for research and drafting

Location & Work Authorization

• Location: Hybrid - we’re in the office in Palo Alto, CA near the Caltrain station from Tuesday to Thursday, with Mondays and Fridays remote.

• Work Authorization: At this time, we are unable to sponsor new visas, but we encourage you to check back soon, as this may change.