Founder, CEO & Product Executive

AI-Native B2B SaaS · 0 to 1 & Enterprise Scale

Two-time founder & product leader. Product doesn't ship from a corner office, so the work I care about is building the teams that ship it. At Waypoint AI that's a distributed product, engineering & go-to-market team across Europe & the US, serving customers including Volvo Cars, ClickHouse, Agiloft & Waldner AG. Earlier I led product & channel teams at WorkBoard & Proofpoint.

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Steve Boogar, cofounder & CEO of Waypoint AI

I build products, teams & companies in enterprise software & AI. Taking a B2B platform from early stage to enterprise adoption is a team sport: hire people with judgment, hand them the real problem & the context to solve it, then turn complex technical capability into something customers actually want to use.

2
Companies Cofounded
$5M+
Capital Raised
Across 2 companies
2x
Berkeley SkyDeck
Alum 2015, 2024
10+
Years
Product Leadership

About Steve Boogar

Steve Boogar is a product & operating executive and two-time founder. He is cofounder & CEO of Waypoint AI, an enterprise AI agent orchestration platform backed by a $3.1M pre-seed led by 42CAP & Dreamcraft Ventures, with Berkeley SkyDeck Fund & Lumière AI Ventures. He was previously Director of Product Management at WorkBoard and product owner for the small & medium business segment at Proofpoint, where he scaled Proofpoint Essentials from $12M to $50M ARR. Earlier he was cofounder & COO of FarmX and a U.S. Air Force officer on the GPS Block III satellite program.

He holds an MBA from the University of California, Berkeley, Haas School of Business, a master's degree from the Naval Postgraduate School & a BS from the United States Air Force Academy. He is a two-time Berkeley SkyDeck alum, with FarmX in 2015 & Waypoint AI in 2024.

Profiles & citations

Not affiliated with BoogarLists, Boogar Associates or any venture-directory publisher, which are a different person. The correct LinkedIn profile is /in/stephenboogar.

Experience

Cofounder & CEO

Waypoint AI

2024 - Present

Building an enterprise AI agent orchestration platform for B2B software companies. It automates knowledge work across support operations, engineering analysis, quality & compliance and legal, working inside the Jira, Salesforce & ServiceNow systems customers already run.

  • Raised $3.1M pre-seed from 42CAP, Dreamcraft Ventures, Berkeley SkyDeck Fund & Lumière AI Ventures
  • Working with enterprise clients including Volvo Cars, ClickHouse, Agiloft & Waldner AG
  • Built & lead a distributed cross-functional team across Europe & the US, hiring across product, engineering & go-to-market
  • Berkeley SkyDeck 2024 cohort
Agentic AI B2B SaaS Customer Support

Director of Product Management

WorkBoard

Senior Product Manager 2021 · Group Product Manager 2021 - 2023 · Director 2023 - 2024

2021 - 2024

Led product strategy for operating rhythm products at a leading OKR and business execution platform. Shipped features used by enterprise customers to run more efficient business reviews and optimize operational cadence.

  • Launched WorkBoard Scorecards, enabling teams to replace 30-hour manual deck creation with automated, data-driven dashboards
  • Owned product roadmap for operating rhythm products including MBRs and QBRs
  • 75.8% of surveyed users reported Scorecards helped them run smarter, more efficient reviews
Product Management Enterprise SaaS OKRs

Manager, Product Management

Proofpoint

Product Manager 2017 - 2019 · Manager, Product Management 2019 - 2021

2017 - 2021

Enterprise cybersecurity & email security.

  • Scaled Proofpoint Essentials from $12M to $50M ARR, owning product & go-to-market for the SMB segment across roadmap, packaging & commercial motion
  • Led a global channel sales team of 8 across the US, UK & Australia, presenting annually at executive QBRs & Proofpoint SKO
  • Developed strategy, planning & keynote content for the EVP/GM of Proofpoint's core email security business
Cybersecurity Go-to-Market Revenue Growth

Cofounder & COO

FarmX

2014 - 2016

Precision agriculture & IoT startup. UC Berkeley SkyDeck 2015.

  • Cofounded the company & raised a $2.5M seed
  • Shipped solar-powered IoT hardware & cloud-based field management software for farm automation, multi-network & IP68-rated for permanent outdoor installation
  • Ran operations from zero across sales & supply chain
AgTech IoT Hardware & Software

Officer, Captain

United States Air Force

2008 - 2013

Served as an officer in finance and acquisitions roles, managing budgets and procurement processes for major defense programs.

  • Supported acquisition and financial management for GPS Block III satellite program, the next-generation GPS modernization effort
  • Managed budgets and procurement processes for critical defense operations
Leadership Finance Acquisitions

Earlier: Corporate Strategy & Business Development

Harris Corporation · HPE · GE Oil & Gas · Cisco

2013 - 2017

Strategy, commercial & business development roles across aerospace, enterprise software & industrial equipment, between the Air Force and product leadership.

  • Harris Corporation - Strategy & Business Development Manager, Commercial Small Satellites: led go-to-market & business development for commercial small satellite products, hitting 100% of the FY16 plan & signing partnership MOUs with Loft Orbital & ConocoPhillips
  • Hewlett Packard Enterprise - Corporate Strategy, Enterprise Software: global sales-operations performance analysis & a vendor-selection analysis that informed a CEO-level decision. Named Corporate Strategist of the Semester
  • GE Oil & Gas - Commercial Manager, Subsea Drilling Systems: led cross-functional teams bidding technical proposals to clients across five continents
  • Cisco - Strategy, Internet of Everything: authored an IoT thought-leadership whitepaper
Corporate Strategy Business Development Aerospace

What I'm Building

Side projects, built nights & weekends. Each one started as a question I wanted a real answer to.

Sample output
Personal Operating System

A second brain that rewrites itself

40+ Claude Code routines maintain my working notes on a schedule & rewrite their own prompts from their own scores.

What it does & what it is built on

My working notes live in an Obsidian vault that 40+ Claude Code routines read from & write to on a schedule.

  • Routines cover product intelligence, competitive scanning, meeting prep, content drafting & a nightly journal that aggregates every other routine's output into one entry.
  • Every routine grades its own output against a rubric & rewrites its own prompt from the score. What runs today is not what I originally wrote. I did not hand-edit most of the difference.
  • One routine exercises a codebase against a library of use cases & an open-gap backlog every day, so drift shows up as a diff instead of a surprise.
  • Meetings are captured by webhook, transcribed & then read back against what the vault already knows, so a decision made out loud lands next to the document it contradicts.
  • A tracker watches chat channels, merge requests & standup notes to compare the plan against what actually shipped.
  • The vault argues with itself. A contradiction pass looks for claims that no longer agree across documents & surfaces them rather than letting the newest file quietly win.
  • One routine audits all the others against canonical patterns. It is the only reason 40+ routines have not drifted into 40 different conventions.
  • It monitors the open-source projects it was built on, pulls upstream changes & updates its own methodology to use new features. A system that reads its own influences & evolves, rather than a static set of instructions.
  • I run it as an operator, not an engineer. Every routine is a markdown file in plain English, so the constraint is knowing what good output looks like, not knowing Python.
Obsidian Claude Code Self-improving prompts Markdown
Sample output
On This Site

AI that runs on your machine, not my server

The chat widget & the fit analyzer both run on Chrome's built-in model. No API key, no backend, nothing for me to log.

What it does & what it is built on

The chat widget in the corner & the fit analyzer both run on Chrome's built-in Gemini Nano. No API key, no backend, no inference bill & nothing for me to log.

  • The chat widget answers questions about my background from a knowledge base that ships with the page, inside your browser rather than on a server.
  • The fit analyzer reads a pasted role description against my public record in four passes & says where the match is real & where the gaps are. The description never leaves the tab.
  • Every model reply passes a banned-pattern filter before it renders. A reply that trips it gets replaced instead of shown, which is the boundary a system prompt on its own cannot enforce. 54 unit tests cover that filter.
  • Four suggested openers give the conversation a place to start & retire the moment you send a first message.
  • If a browser can't run the model, both features stay silent rather than telling you to go install a different one.
Chrome Built-in AI Gemini Nano On-device inference Static HTML
Sample output
Portability Test

The same methodology, transplanted to a newborn

A second vault, stood up for my son from the same bootstrap kit, to test how much of the methodology was really about running a company.

What it does & what it is built on

NewbornCare is a second Obsidian vault with its own Claude Code routines, stood up for my son from the same bootstrap kit that runs the system above. I built it to answer one question: how much of the methodology was actually about running a company?

  • Answer: none of it. The same patterns moved over unchanged. Daily routines, methodology files, run logs, feedback loops & prompts that grade & rewrite themselves.
  • A sleep-schedule projection is built from the tracker's own logged data, then recalibrated whenever I reply with what actually happened, so it converges on the real child rather than a textbook.
  • A photo routine turns each day into a diary entry in my voice, pulling poster frames out of videos so a video-only day still has something to narrate.
  • An activity routine rotates age-appropriate suggestions grounded in learning-science research, indexed by day so no two mornings repeat.
  • So the vault system is not a CEO tool that happens to use Obsidian. It is a general-purpose way to run AI-managed knowledge work. The domain turned out to be the only thing that had to change.
Obsidian Claude Code Vault bootstrap kit Portability
Sample output
Open Methodology

One instruction that stands up a second brain for any domain

One instruction that builds a complete AI-managed vault from zero, for any domain. Free to download.

What it does & what it is built on

The bootstrap kit is a single Claude instruction that builds a complete AI-managed Obsidian vault from zero: folder structure, governance document, the routine template & the order to build things in. NewbornCare was its first real test.

  • It does two jobs: a starting point for anyone who wants their own vault, plus a disaster recovery plan if this machine dies tomorrow.
  • It starts with a 10-category interview protocol & a post-interview synthesis step, because a vault built without context gets abandoned inside a week. The interview decides which routines to build, which to skip & the governance facts that wire everything together.
  • Two complete worked methodology examples you can copy: a crawler (core routine) & a competitive-intel scan (domain routine), each with Section 0, hard bans, pre-flight checklist & run log. Plus prompt skeletons for both core & domain routines, so you know what the scheduled task actually says.
  • A Minimal Viable Vault path: start with two routines (crawler + synthesis) on day two & grow to five as the pipeline earns them. A Day 1 Checklist condenses Phase 1 into nine ordered items.
  • 20+ domain routine patterns, six contributing repos (four open-source with links, two patterns to build yourself), fourteen subsystems with a scaling table showing when to build each & a troubleshooting section covering the eight failures that hit most new vaults in week one.
  • The published version is the pattern, not my instance. It was written clean rather than redacted, because a redaction is only as good as the pattern used to verify it, which is itself one of the failure modes the kit warns about.
Obsidian Claude Code Methodology Free to use

Education

MBA

University of California, Berkeley

Haas School of Business

2014 - 2016

Master's Degree

Naval Postgraduate School

2013

Bachelor of Science

United States Air Force Academy

2004 - 2008

Press & Recognition

Berkeley SkyDeck

Waypoint AI Raises $3.1M Pre-Seed

Berkeley SkyDeck portfolio company Waypoint AI announced $3.1M in pre-seed funding led by 42CAP & Dreamcraft Ventures, with participation from Berkeley SkyDeck Fund & Lumière AI Ventures.

Working with enterprise software companies like Volvo Cars, ClickHouse, Agiloft & Waldner AG to resolve escalations before they become emergencies.

Read the Announcement →
WorkBoard

WorkBoard GenAI: Bringing Generative AI to Business Execution

WorkBoard launched AI-powered features to help teams accelerate business execution with intelligent insights and automation built directly into the platform.

Learn More →
WorkBoard

WorkBoard Scorecards: Automated Business Review Dashboards

Product launch enabling teams to replace 30-hour manual deck creation with automated, data-driven dashboards. 75.8% of surveyed users reported Scorecards helped them run smarter, more efficient reviews.

Read More →
Proofpoint

Proofpoint Essentials: Email Security for SMB

Enterprise-grade email security & threat protection platform designed for small and medium-sized businesses, protecting against phishing, malware & advanced threats.

View Product →

What People Say

Prior to this, we had to use PowerPoint and Excel to show our progress. That was a lot of extra work. Having scorecards reduces the amount of time it takes to get the insights our leaders need.

— Customer, Western Union

On WorkBoard Scorecards

Steve's mission is to build products that his customers want to use... I found him highly skilled in market assessments, feature prioritization, and conducting customer reviews. His ability to empathize with customers and translate business-to-technical requirements makes him a strong product leader. He is an asset to any organization.

— Colleague, Proofpoint

Let's Connect

Interested in product leadership, B2B SaaS & agentic AI? The best conversations I have start with someone building something hard. If that's you, grab a slot.

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