This post originally appeared on my blog. After spending a few months marketing to enterprises with both a field and inside sales team, I have some thoughts on marketing to Enterprise vs SMB and what it means for a CMO. (Don’t read anything into this. …

After taking a year to explore the Boston tech community and figure out what I want to do next professionally, I learned a lot about myself and the ecosystem as a whole. One big hole in our ecosystem is pillar companies — companies big enough to make large acquisitions, create…

We have completed our first investment as Operator.vc in a company called Privy, where we were the lead investor in a small(ish) new round of financing (Privy official announcement). We are big believers in the company because the grit the team has displayed and their amazing metrics. …

One hard part about investing is that you have to pass on good companies and good people — you say “no” a lot. One hard part about being a founder is that people say no when you try to recruit them, customers say no when you try to sell to…

At SaaS and other b2b tech companies, hiring BDRs to send more and more emails seems to be all the rage, and now there are tools that let those BDRs send thousands of “personalized” emails automatically each day. With the rise of all the automated cold email prospecting tools, there…

Article originally published on Mike Volpe’s blog. If you boil down to the essence, there are really only two business models. Better Mousetrap — You are entering an existing market with a product that is better than the existing solutions in some way — could be cheaper, faster, stronger, easier…

Adapted from a blog post “Why Quarterly Businesses are Doomed” — read original full version. Biologists study fruit flies because their 30 day lifespan means you can study multiple generations quickly. While building HubSpot, we ran the business monthly, not quarterly. Marketing goals were monthly. Sales goals and commissions were monthly. We produced financial and other reports monthly. And most importantly we made changes to marketing, sales and the product roadmap monthly.

After doing marketing for 15+ years and eventually being CMO of a team of 100+ marketers, I think I know something about marketing. In my current role as board member, advisor and investor, I often talk to companies about their marketing. We brainstorm ideas, review metrics, and put plans in…

We’re in the middle of some big changes in corporate culture and work environment. There is a movement at companies toward more internal transparency of information and autonomy of work. If you do it right, you can unlock some amazing performance from your team or company. Transparency of information: When…