Founding Chief of Staff, GTM + Operations

Humanity should not keep paying the cost of knowledge it has already created.

Autostep measures outcomes from human and AI work, identifies what companies should change, and helps make that change happen.

We have real customer pull. Your job is to expand that demand, set qualified meetings, help create exceptional outcomes for the customers already working with us, and put structure around everything required to make that happen.

This is not a strategy-and-slides Chief of Staff role.

You’ll work across GTM and operations, alongside the CEO who closes deals. A major part of your job will be outbound prospecting and setting qualified meetings with mid-market and enterprise companies.

• Prospect consistently: research companies and people, build lists, develop campaigns and copy, run personalized outbound across channels, follow up, and set qualified meetings for the CEO to close. This can include highly personalized hand-written outreach, scaled email campaigns, LinkedIn outreach and content, cold calls, and other channels that reach the right buyers.

• Think of and run GTM experiments across messaging, audiences, campaigns, channels, and positioning. Track what happened and adjust.

• On prospect conversations, ask concise, relevant questions, listen closely, probe when needed, understand the outcome that matters, and drive toward the right next step.

• Work directly on helping create as much value as possible for our clients and keeping customer commitments moving.

• Take messy requirements and arrangements and turn them into clear owners, next steps, deadlines, and systems.

• Move proposals, contracts, compliance requests, follow-ups, renewals, and other deal/customer work forward.

• Build and maintain the systems of record the company needs across pipeline, customers, contracts, experiments, recruiting, and operations. Decide what should be tracked, keep it current, and make sure the company can actually rely on it.

• Build automations and agents.

• Draft high-quality outreach, LinkedIn content, copy, and proposals; help update landing pages; coordinate contractors and recruiting work; and step into whatever is blocking a customer or revenue.

• Recognize risk, prioritize correctly, and escalate the things that actually matter.

A history of personally driving outcomes, not just advising other people on what to do.

Ability to identify the right audience, develop the message, build the list, and execute high-quality personalized outbound across channels. You can write outreach by hand when personalization matters, use tools like Instantly or Smartlead when scale matters, pick up the phone when that is the best channel, use LinkedIn effectively, run the experiment, and understand the result.

Ability to take something disorganized and turn it into a clear, executable plan.

Ability to take scattered information across conversations, documents, tools, and people and turn it into a clear system of record that stays current.

Comfort talking to executives and customers, with the judgment to ask concise, relevant questions, probe when needed, and actually listen to the answer.

Hands-on experience building automations and agents.

Enough technical curiosity to learn deeply about AI, ML, LLMs, agents, and automation while remaining commercially oriented.

Strong judgment, unusually high learning rate, great communicator, and enough independence that every problem does not come back to the CEO.

You will learn an enormous amount across enterprise GTM, customer delivery, AI, operations, contracts, compliance, recruiting, automation, product, and how an early company actually gets built.

You’ll work directly alongside a founder who has worked across AI/automation and multiple seed-to-Series A startups, inside a company backed by YC and Neo.

You’ll also work alongside investors who advise us, including Walden Yan (Co-Founder, Cognition, $26B), Erik Goldman (Co-Founder, Vanta, $4B), Charles Mourani (Co-Founder, Cherry, $2B), Kabir Barday (Co-Founder, OneTrust, $4.5B), and Kunal Shah (CEO of WhatsApp; Co-Founder, CRED, $4.5B), alongside other reputable enterprise founders and co-founders.

This will be hard. We expect high ownership, speed, and measurable outcomes.

There is a real chance to help change the way work gets done.

Customers get exceptional value.

Proposals and contracts move.

Qualified meetings get booked.

Prospects move.

Nothing important disappears because it was sitting in somebody’s head.

Experiments produce answers.

The company gets more organized as it moves faster.

And the work you're doing helps turn customer demand into a repeatable business.

AI Agents · Prompt Engineering · Data Analytics · Prototyping · Outbound Prospecting · Outbound Sales · Personalized Outbound · Enterprise GTM · Enterprise Sales · Account Research · Campaign Strategy · Cold Email · Cold Calling · LinkedIn Outreach · LinkedIn Content · Written Sales Outreach · Multi-Channel Prospecting · CRM · Sales Operations · Customer Success · Systems of Record · LLMs · LLM Workflows · AI Automation · Agent Building · Workflow Automation

Phone Screen

References

In-Person Working Interview(s) in San Francisco (IRL Preferable / Virtual Options)

GTM and Customer Simulation

Operations and Automation Simulation

Final Conversation