Enterprise Weekly #551: AI Founders Build Different, and More

Work-Bench is a NYC-based $160M enterprise software Seed stage VC fund. If you are or know anyone thinking about founding an enterprise software, SaaS, or infrastructure software startup - we’d love to meet! Please reach out to chat.

For many mature enterprise software companies, they know the AI opportunity ahead of them is do or die.

This week, Eoghan McCabe, co-founder and CEO of Intercom, published one of the most candid essays we’ve seen from a SaaS CEO. Data points from it? Intercom is now at $400M ARR, with their AI agent Fin crossing $100M ARR on its own and growing at ~3.5x. But what’s interesting and universally applicable is the work Intercom had to go through to get there.

Some of what Intercom destroyed to rebuild:

• Rewrote their mission, values, and hiring criteria from scratch

• Moved 80% of R&D onto Fin while it was still a single-digit percent of revenue

• Actively killed ~$60M ARR by overhauling their pricing model

• Spent $1M on a .ai domain and redirected 100% of paid traffic to it

• Grew their AI team from ~6 to ~60 people in three years

Eoghan isn’t alone in taking such a drastic effort to resteer the ship! The same pattern is playing out at Box and Amplitude: two founder-led public software companies that see going all-in on AI as necessary to survival.

Aaron Levie at Box knows what’s at stake: “You can just see how the AI tsunami could wipe you out if you make just two, three, four, five wrong decisions in this space.” In response, Aaron has reorganized Box around a startup-within-a-company focused entirely on agents: a team he describes as “the make or break on everything related to AI agents”.

Spenser Skates at Amplitude tells a similar story. Amplitude ran two full reorganizations of their engineering, product, and design org in a single year, moving out leaders who were “very much in the SaaS modality but not on the bleeding edge of AI.” He describes the mindset shift required: “As a founder, your job is always to run to the most difficult problem in the business and lead from the front.”

A few things we find striking across all three:

• Desperation is an asset. All three had a forcing function: Intercom’s near-negative growth, Box’s existential threat from agents, Amplitude’s board pressure and competitive squeeze. The urgency unlocked courage that complacency never could.

• The founder had to personally re-engage. None of them delegated this wave. Eoghan returned to the CEO seat. Spencer ran AI week himself and was the primary change agent. Aaron splits his management philosophy cleanly: 70-80% of Box he touches about 5% of, “and then there’s this part that is like the existential part of the business, which is if we don’t do this right, we’re out of business.” The lesson: this moment requires the principal, not a proxy.

• They committed before the economics justified it. Intercom moved 80% of R&D to Fin while it was a rounding error on revenue. Amplitude launched dedicated AI teams when AI products were still side projects. Box called their agent initiative existential and organized accordingly before agent revenue showed up. The early commitment is what’s producing the asymmetric results today.

Very interesting times in enterprise software land. Will be fascinating to see how decisions made by today’s founders and CEO play out over the next 3-5 years!

💡 Work-Bench Masterclass: Using AI for Startup Market Discovery (Mar 18): Join us for a Work-Bench Masterclass with our Venture Partner, Diego Oppenheimer, where he’ll walk through a practical framework for using AI to research markets and evaluate startup ideas. Sign up here.

🚀 Best of NYC with Work-Bench: Bar Snack (March 18): We have a few more spots for our Best in NYC drinks, bringing together NYC’s best operators across product, sales, engineering, growth, and more. See here for more.

♠️ NYC Tech Poker Night with Work-Bench and Courier Health (Mar 25th): Work-Bench and Courier Health are hosting a fun, poker night for NYC founders and operators. This will be an intimate 30-person event. Sign up to play here.

📚 Read more news:

• WSJ: Broadcom’s AI Business Is Booming. The Rest Is Complicated.

• TechCrunch: AWS launches a new AI agent platform specifically for healthcare

• VentureBeat: OpenAI launches GPT-5.4 with native computer use mode, financial plugins for Microsoft Excel, Google Sheets

• CNBC: Morgan Stanley’s top tech banker: It’s ‘wartime, not peacetime’ for software

• Reuters: OpenAI tops $25 billion in annualized revenue, The Information reports

🧵 Read more threads:

• Jessica Lin: Tactical GTM Tips from Chris Pisarski

• Jon Lehr: Work-Bench Masterclass with Diego Oppenheimer on AI for Market Research

• Danny Chesley: Takeaways on How The Best Founders are Using AI

• Natalie Marcotullio: Helping Out as a Work-Bench Advisor

• Cursor: PlanetScale protects production reliability with Bugbot

Company: GovWell
Role: AI Product Engineer
Technology: Modern Software for Governments
Funding: $5.5M from Work-Bench, Bienville Capital

🌟 Company of the Week 🌟
Cotool raises $7.4M led by a16z
Risk / Security • Seed • San Francisco, CA
Founders: Max Pollard, Logan Carmody, Eddie Conk

Vivox AI Raises $1.5M led by Axel Weber, Dan Cobley, and Others
Future of Work • Seed • London, UK

Diligent AI raises $2.5M led by Speedinvest and Shapers
Risk / Security • Seed • London, UK

14.ai raises $3M led by Y Combinator
Collaboration / Productivity • Seed • San Francisco, CA

IntelliGRC raises $3.5M led by Kyle Hanslovan and Blu Ventures
Risk / Security • Seed • Fairfax, VA

Plurio raises $3.5M led by Altair, DVC, and Others
Sales / Marketing • Seed • San Francisco, CA

Tangled Raises $4.5M led by byFounders
Infrastructure / Dev Tools • Seed • Copenhagen, Denmark

Inhouse raises $5M led by Run Ventures and Royal Street Ventures
Future of Work • Seed • Los Angeles, CA

Akave raises $6.65M led by Protocol Labs, No Limit Holdings, and Others
Infrastructure / Dev Tools • Seed • Wilmington, DE

Confido raises $9M led by Aquiline Capital Partners
Future of Work • Venture • Seattle, WA

Firmable raises $14M led by Airtree
Sales / Marketing • Series A • Melbourne, Australia

ArmorCode raises $16M led by Cheyenne Ventures
Risk / Security • Venture • Palo Alto, CA

Evervault raises $25M led by Ribbit Capital
Data / AI / Machine Learning • Series B • New York, NY

Reclaim Security raises $26M led by QP Ventures, IBEX Investors, and Acrew Capital
Risk / Security • Seed & Series A • New York, NY

Lio raises $30M led by A16z
Collaboration / Productivity • Series A • New York, NY

Validio raises $30M led by Plural
Data / AI / Machine Learning • Series A • Stockholm, Sweden

JetStream Security raises $34M led by Redpoint Ventures
Risk / Security • Seed • San Francisco, CA

Unleash raises $35M led by One Peak
Infrastructure / Dev Tools • Series B • Oslo, Norway

Fig Security raises $38M led by Team8 and Ten Eleven Ventures
Risk / Security • Seed & Series A • New York, NY

Guild.ai raises $44M led by GV
Data / AI / Machine Learning • Seed & Series A • San Francisco, CA

Cylake raises $45M led by Greylock
Risk / Security • Seed • Sunnyvale, CA

ZyG raises $58M led by Bessemer Venture Partners, Viola Ventures, and Lightspeed Venture Partners
Sales / Marketing • Seed • Tel Aviv, Israel

WorkOS raises $100M led by Meritech and Sapphire
Infrastructure / Dev Tools • Series C • San Francisco, CA

Ayar Labs raises $500M led by Neuberger Berman
Data / AI / Machine Learning • Series E • San Jose, CA

Accenture acquires Ookla for $1.2B
Infrastructure / Dev Tools • Acquisition • Seattle, WA