Ideal VC Board Member: Five Essential Traits
If I had my pick of VC’s in my next round, I’d look for a “5 tool board member:” 1. Works at a top tier firm 2. Is a GP 3. Has relevant domain expertise 4. Has been an operator 5. Not an a-hole What am I missing?
Five CEOs Master Vision, Code, Taste, Sales, Recruiting
What do @btaylor (Sierra), @matistanis (11Labs), @kareem (Clay), @parkerconrad (Rippling), @GabeStengel (Rogo), & @daraladje (Delphi) all have in common? They are 5 tool CEO's: (1) Vision, (2) Code, Taste (3), Sell (4), & Recruit (5). Learn more on this...
Companies Shift Gravity: From Employees to Customers, Acquisition to Delight
I think all companies have two centers of gravity 1. Focused on investors, customers, or employees 2. Focused on acquiring or delighting customers HubSpot moved (1) from employees to customers over time. We moved (2) from acquiring to delighting over...
Old CEO Playbook Broken; New Strategies Unveiled
Ye olde CEO playbook I used in building @HubSpot is broken. From Jensen Huang’s 60 direct reports to the way Elon runs his empire to Brian Chesky’s founder mode – it's a reboot. This new playbook is something I’m very curious...
From Starter to Scaler: Evolving Sales Leadership Stages
In the startup to scaleup journey, I often see 3 phases of sales leaders: Starter - A leader who can hire a few reps and close some deals. High Riz. Closer. Not analytical. Solver - A leader who can figure out the profile of...
Startups Advance in Small Leaps, Not Silver Bullets
Startups are 1 step back, 2 steps forward, 1 step back, 2 steps forward, etc. From the outside, HubSpot might seem like a smooth up-and-to-the-right story. It belies what actually goes on inside. The best way I’d describe HubSpot is two...
Leadership Improves When You Stop Pretending to Know Everything
For a very long time as CEO of HubSpot, I thought I was supposed to have all the answers. Life got easier for everyone (especially me) when I got over that.
Scale Smart: Hire Slow, Promote Internally, Balance Talent
A lot of startups get stuck in the mud between 200 and 2000 employees. Here are my tips: 1. Ye old "hire slow and fire fast" is still true. 2. Push off the director layer as long as you can....
From Seats to Credits: Next Bubble's Lingering Hangover
There was a “seats” hangover after the 2021 bubble There will be a “credits” hangover after the 2025 bubble
Customer Sales Feel Better than Investor Pitches
Selling to customers is so much nicer than selling to investors.
Build Friendships with Competitor CEOs for Founder Success
I always tried to keep a good relationship with the CEOs of HubSpot’s competitors, like Salesforce, Zendesk, Marketo, Eloqua, Mailchimp, etc. It served us well. I recommend founders do the same.
Take Acquisition Offers Seriously—High Valuations Favor Selling
Dear Founders, If you have acquisition interest from a bigger co, take it very seriously. If you don’t sell, that bigger co will buy your competitor or build. Not great for you. Also, valuations are sky high right now,...
SF Tech Firms Adopt New Ideas Far Easier than Others
Getting tech companies in San Francisco to try your new thing is A LOT easier than convincing the other 99% of companies out there.
Hyper-Growth Inevitably Triggers Churn, Then Sustainable Second Act
I predict this cycle for a lot of the hyper-growers: 1. Hyper-growth 2. Massive churn crisis 3. Fix churn crisis 4. Growth 5. 2nd Act
Outcome‑Based Pricing Unlikely to Go Mainstream
I was really excited about the outcome based pricing model à la what Sierra, Fin, etc are doing, but the more I look into it, the more I think it won’t become the norm. Too hard to apply in...
Prioritize Delighted Customers over Hype Growth Curves
Dear Hyper-growth founders, Legendary companies are built on the backs of their delighted customers, not on the backs of their buzz/curves/demos. Don't fall in love with your hockey stick curves...fall in love with your customers. Love, Brian.
Transparent Prep and Dialogue: CEO Board Meeting Essentials
Board meeting tips for CEO's of private companies: 1. Be transparent -- it builds trust. Board members can tell if you are spinning them. Save the sales pitch for the sales prospect. 2. Prep time -- Either send...