Scaling a startup doesn’t just test your business model, it tests you as a leader. The skills that helped you build your company from the ground up aren’t always the ones that will carry it forward. As teams expand, decisions get more complex, and expectations rise, founders must evolve from doers to leaders - learning to communicate vision, delegate effectively, and build systems that empower others to excel. Recorded live at Startup Boston Week 2025, this session dives into

Last night, we hosted our third FounderConnect with CIC’s Social Impact Program, bringing together founders and resource partners who are fueling Boston’s startup community. The energy in the room was incredible, founders connecting with accountants, HR pros, developers and advisors all focused on one shared goal: helping startups build smarter, stronger, and faster. Each company and organization represented offers a different piece of the startup puzzle - from tax and legal

Author: Derek Fieldhouse, Customer Success Manager, Fidelity Private Shares Raising your first or second round is a major milestone that you want to be prepared for. It is perhaps the first time you will have outside investors scrutinizing every detail of your company, especially your cap table. A messy or inaccurate cap table can slow down diligence or even scare investors away. As someone who’s worked with numerous companies through their seed rounds, I’ve seen how a clean

Authored by: Matt Shrimpton & Bob Baker, Partners at Peak Corporate Counsel Startups need money, and usually a lot of it. Building a team and an MVP can get expensive, and at some point in the lifecycle of most startups, they will seek outside capital. Most of these raises will involve equity financing – receiving money in exchange for a percentage of ownership in the company. Investors will want to put their money in a business which provides a unique and valuable product o

Listening to your customers isn’t just good practice, it’s your greatest growth strategy. A thoughtful Voice of the Customer (VoC) program turns feedback into focus, helping startups make smarter product decisions, deepen trust, and build lasting relationships. Whether you’re just starting to collect feedback or looking to formalize your process, this session dives into how to design a VoC program that fits your stage, your team, and your goals. Recorded live at Startup Bosto

Building a great product is about more than hitting product-market fit - it’s about staying there. Between customer demands, feature requests, and market shifts, founders are constantly adapting to build products that resonate, scale, and stand the test of time. At Startup Boston Week 2025, founders, product leaders, and investors came together to explore what it really takes to build products that win, not just once, but over and over again. These conversations unpack how to

As your startup scales, your board can either accelerate your growth, or slow it down. The difference often comes down to how well you manage the relationship. From aligning expectations and preparing for tough conversations to turning board feedback into strategic advantage, this session dives into what it really takes to build and lead a high-performing board. Recorded live at Startup Boston Week 2025, this discussion explores the evolving role of the board through the lens

Being an underrepresented founder in the startup world often means navigating invisible barriers while building something new. But it also comes with a deep well of resilience, creativity, and community. At Lifting as We Climb, with Startup Boston and City of Boston, founders and investors came together to talk candidly about the realities of representation - and how we can all play a role in building a more inclusive ecosystem. The panel last night featured Farah Hussain  (E

Understanding how to structure and manage equity can make or break a startup’s future. Whether you’re dividing shares with co-founders, bringing on early hires, or preparing for your first funding round, equity decisions shape not only ownership - but alignment, trust and long-term growth. In this session from Startup Boston Week 2025, our panel of founders and experts unpack the fundamentals of equity management: how to split equity fairly, design vesting schedules that work