Bring Your Burning Founder Question to Startup Boston Week 2026

What’s the one thing keeping you up at night as a founder?

Maybe you’re struggling to find product-market fit. Maybe fundraising has stalled. Maybe you know you need a better sales process, but you’re not sure where to start. Or maybe the biggest challenge is simply figuring out what deserves your attention next.

On Friday, September 18, during Startup Boston Week, we’re bringing founders together for Mentor Groups: small-group conversations designed to help you dig into the challenge that’s actually on your mind.

There are no presentations and no sitting quietly in the back of the room. Instead, you’ll join an experienced mentor and a small group of fellow founders around a specific topic or challenge. Come prepared with your one burning question, talk it through with the group, learn from what others are navigating, and leave with new perspectives and practical next steps.

Here are the mentors joining us this year and the conversations they’ll be leading and don’t forget to grab your free ticket right here to attend! 

On Friday, September 18 @ 10am - 11:30am

Sales Process with Julie Meyer

If you know you need a more intentional approach to turning prospects into customers, Julie Meyer, Founder + Principal of Connection151, will lead a group focused on building a stronger sales process.

Julie has spent her career building B2B consulting businesses and helping business owners connect with their most valuable customers. She founded Eat Well Global, growing it into a global team of nearly 30 working with many of the Fortune 100’s largest food companies, and later co-founded AugMentors. Today, through Connection151, she works with B2B business owners on growth strategy and customer acquisition while also teaching entrepreneurship and innovation at Northeastern University and Tufts University.

Bring your question about: building a repeatable sales process, landing valuable customers, moving prospects forward, or figuring out where your sales motion is breaking down.

Product-Market Fit with Ying Chen

Finding product-market fit rarely happens in a straight line. Ying Chen, Chief Product Officer & GM at Accelrion, knows what that messy middle actually looks like.

Ying has built and scaled products and businesses across startups and public companies, with experience spanning MIT Media Lab spinout Luminoso, HubSpot, and two successful startup exits. Along the way, she has worked through customer discovery, product-market fit, and building go-to-market motions that can actually scale.

Bring your question about: finding or validating product-market fit, understanding what customers really need, deciding what to build next, or translating early traction into something repeatable.

Fundraising with Sofia Aguilera

Fundraising gets a lot easier when you understand how investors actually evaluate startups.

Sofia Aguilera, Senior Innovation Associate at SVG Ventures THRIVE, leads technical evaluation and innovation initiatives connecting startups with global corporate partners. She is the lead author of THRIVE's Top 50 AgTech and FoodTech reports and serves as a primary reviewer for its Global Impact Challenge.

Previously, Sofia was an Associate at AgFunder, where she sourced and diligenced agrifoodtech startups. She brings an investor's perspective to understanding what makes a company stand out and what raises questions during evaluation.

Bring your question about: preparing to raise, investor positioning, telling your story, understanding diligence, or figuring out what investors may see when they evaluate your company.

Leadership & Prioritization with Patrick Brand

There will always be more things a founder could do than there are hours in the day. The hard part is deciding what matters most and communicating those decisions when the stakes are high.

Patrick Brand, Principal at Excelsa Consulting, is a Chief of Staff who helps leadership teams navigate fundraises, acquisitions, reorganizations, pivots, and other high-stakes moments.

Previously, he was employee #1 and Chief of Staff at a venture-backed edtech company, where he led fundraising processes from research and funnel-building through decks, data rooms, and diligence while helping scale the company to 150+ employees and 100+ enterprise customers.

Bring your question about: prioritization, navigating a high-stakes decision, aligning your team, communicating through change, or figuring out what deserves your attention right now.

Marketing Strategy with Oksana Matviichuk

If you’re trying to figure out how your marketing strategy needs to evolve — especially as AI changes how companies operate, compete, and grow — Oksana Matviichuk, Founder + CEO of OM Strategic Forecasting, will lead a group focused on building a smarter, more intentional marketing strategy.

Oksana brings 20 years of marketing and advertising experience, including strategy leadership within Publicis and WPP, where she developed strategy for Fortune 50 and Global 500 brands including IBM, Dell, Verizon, Lenovo, AWS, and Ford. Today, through OM Strategic Forecasting, she helps founder-led companies rethink their business and growth strategies for an AI-native world. She’s also a USA Today bestselling author and Forbes contributor with more than 100 published features.

Bring your question about: sharpening your marketing strategy, figuring out where to focus your resources, using AI more strategically, differentiating your company, or building a growth approach that can actually scale.

On Friday, September 18 @ 12:30pm - 2:00pm

Product-Market Fit with Seema Sheth-Voss

Sometimes the product is strong, but the market still isn't responding the way you expected.

Seema Sheth-Voss, GTM Advisor at Protobi, works hands-on with early- and growth-stage startups to bring clarity to complex products, particularly across data, AI, deep tech, and SaaS.

Her experience spans PMF and ICP discovery, positioning, product marketing, demand generation, sales alignment, and the systems connecting all of it. She specializes in helping teams figure out where their GTM motion is getting stuck and what they should actually do next.

Bring your question about: ICP, positioning, messaging, customer traction, GTM experimentation, or figuring out whether your challenge is really the product, the market, or how you're connecting the two.

Fundraising with John Newkirk

What actually happens on the other side of the fundraising table?

John Newkirk, Investment Associate & Portfolio Manager at Kamay Ventures, has screened more than 700 startups, led full due diligence processes, and supports a portfolio of 20 companies on fundraising strategy, data room preparation, and investor positioning.

His work also sits at the intersection of startups and large corporations. Through 70+ sessions with executives and business leaders, he has helped translate corporate pain points into more than 200 pilot designs and commercial partnerships.

Bring your question about: fundraising strategy, investor outreach, preparing your data room, navigating diligence, positioning your company, or selling into large corporate partners.

Leadership & Prioritization with Farah Hussain

As your startup changes, the way you lead has to change with it.

Farah Hussain, Founder & Executive Coach at Coaching with Farah, works with leaders on executive presence, decision-making, and communication. She brings nearly 20 years of global industry experience, including senior roles at PayPal through its IPO, hypergrowth, and multiple restructures.

Over the past seven years, she has coached founders and teams from pre-seed through Series D as they navigate pivotal moments in their companies' growth.

Bring your question about: making difficult decisions, communicating as a leader, managing competing priorities, leading through uncertainty, or becoming the leader your next stage requires.

Customer Discovery with Chris Murphy

You can build the perfect sales process on paper, but it doesn't matter if you aren't solving a problem customers care enough about.

Chris Murphy, President & Senior Advisor at Wentworth Sales Consulting LLC, has spent his career in sales and sales leadership across SaaS companies, including small venture-backed startups. He has built and grown sales teams around the world and managed hundreds of salespeople.

Today, he works hands-on with small and mid-sized businesses to assess their sales operations, identify what's getting in the way of growth, and build the processes, tools, and teams needed to improve results.

Bring your question about: talking to prospective customers, understanding what buyers actually need, validating assumptions, turning discovery into sales conversations, or figuring out why prospects aren't converting.

Building an MVP with Sheri Palazzo

How much do you actually need to build before you can put your idea in front of the market?

Sheri Palazzo, Founder of Saplings Consulting, brings more than 30 years of engineering experience from HP, GE, Bose, and multiple startups. Through Saplings Consulting, she helps startups navigate technical leadership, program management, team development, manufacturing, and operations.

Sheri has supported more than 50 startups and has served as an Expert-in-Residence at Greentown Labs, MassChallenge, and Boston University. She is also a Board Member at FORGE and an active mentor across university, accelerator, and incubator programs.

Bring your question about: defining your MVP, deciding what to build first, balancing speed and technical complexity, moving from prototype toward production, or figuring out what not to build yet.

Your Question Is the Agenda

Mentor Groups aren't designed around generic advice. They're designed around what founders in the room are actually navigating.

That means the value of the conversation starts with what you bring to it.

Come with the question that's been sitting in the back of your mind. The decision you keep going back and forth on. The part of the business where you're stuck. The thing you'd love to talk through with someone who has been there before.

Then spend 90 minutes working through it alongside an experienced mentor and other founders who may be wrestling with many of the same challenges.

Startup Boston Week runs September 14–18, 2026 and is completely free to attend.

Join us Friday for Mentor Groups and bring the one thing that's keeping you up at night.