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Joe Caprio posted thisHey folks :) I’m hosting a small event for Bentley Alum, next Thursday after work, at the Glasswing VC office on Newbury Street. Bentley has launched an entrepreneur’s hub on campus and they’re building pathways for Bentley students into startups. I wish someone gave me this life hack when I graduated. It would have saved me some wasted years in my early career. They’re looking for Bentley alum in Tech, Innovation, and Entrepreneurship to get involved with the club.. judge pitch competitions, give career advice, poach entry level hires 👀, etc etc Dm me if this is you :)
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Joe Caprio shared this..been a while -but I don't really have a "network" in the campground industry that would appreciate a well executed campaign like this. Is it still socially acceptable for people to come here just to brag like this? 😩
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Joe Caprio shared thisHey friends.. seems the world’s gone crazy. Maybe come chill out this summer?
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Joe Caprio shared thisKim wrote a very nice article about our recent decision to leave tech to run a campground in Southern New Hampshire. This means it's unlikely you'll find me on li as much anymore. But there are some people I wanted to thank for their time with me along the way. Follow our website or my tiktok if you want to see us renovate the 50yr old campground 😎Joe Caprio shared thisWe're excited to start our 2nd season of ownership this May. We hope you'll come enjoy the river with us.
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Joe Caprio shared thisI’ve done a lot with my friends at 30 Minutes to President's Club over the years because they do great content and they’re fun to work with.. fun to listen to. They do great content because they relentlessly get in contact with existing SMEs and pack the interviews with great questions - things like “top three mistakes” and “top five tips” on the topic. They feed these questions to the guest as a pre-read and the result is usually really strong and prepared guests with killer insights. This is why all salespeople should pick up their latest effort. It’s on sale for one dollar. You can’t lose!Joe Caprio shared thisFrankly, I didn't think I'd be in sales at all. Somehow, today I'm releasing a sales book. I was a pretty quiet kid growing up. Like many people, I stumbled into sales -- I applied to a finance internship and it turns out it was an internship selling insurance. Next thing you know, they said: "𝐏𝐮𝐭 𝐭𝐨𝐠𝐞𝐭𝐡𝐞𝐫 𝐚 𝐥𝐢𝐬𝐭 𝐨𝐟 𝟐𝟎𝟎 𝐩𝐞𝐨𝐩𝐥𝐞 𝐚𝐧𝐝 𝐜𝐚𝐥𝐥 𝐭𝐡𝐞𝐦." Most folks made a few calls, then said screw this. - Day in... 20 reps left. - Week in... 10 reps left. - Month in... 2 reps left. 𝐀𝐟𝐭𝐞𝐫 𝐚 𝐦𝐨𝐧𝐭𝐡 𝐨𝐟 𝐫𝐞𝐣𝐞𝐜𝐭𝐢𝐨𝐧, 𝐈 𝐬𝐭𝐢𝐥𝐥 𝐡𝐚𝐝𝐧'𝐭 𝐛𝐨𝐨𝐤𝐞𝐝 𝐚 𝐬𝐢𝐧𝐠𝐥𝐞 𝐦𝐞𝐞𝐭𝐢𝐧𝐠. But I stuck around because I was broke and needed the cash. A top rep felt bad for me and took me under his wing. He taught me the "Heard The Name Tossed Around" cold call opener and that quiet kid started to find some success: - 200 dials, 1 meeting - 200 dials, 2 meetings - 200 dials, 4 meetings - 200 dials, 6 meetings I couldn't believe it. At that point, I realized sales meant much more to me than a paycheck. 𝐒𝐚𝐥𝐞𝐬 𝐚𝐥𝐥𝐨𝐰𝐞𝐝 𝐦𝐞 𝐭𝐨 𝐜𝐨𝐧𝐪𝐮𝐞𝐫 𝐭𝐡𝐞 𝐛𝐢𝐠𝐠𝐞𝐬𝐭 𝐛𝐞𝐚𝐬𝐭 𝐢𝐧 𝐦𝐲 𝐥𝐢𝐟𝐞 𝐡𝐞𝐚𝐝-𝐨𝐧: 𝐭𝐚𝐥𝐤𝐢𝐧𝐠 𝐭𝐨 𝐩𝐞𝐨𝐩𝐥𝐞. If you can learn to call strangers, you can learn to talk to anyone. And as someone who is *NOT* naturally talented, I had to break down every single step of the cold call into tiny pieces: - Opener - Problem Proposition - Objection - Voicemail - Gatekeeper The deeper I went, the more success I found. 𝐀𝐧𝐝 𝐭𝐡𝐞 𝐦𝐨𝐫𝐞 𝐭𝐡𝐢𝐬 𝐜𝐨𝐧𝐟𝐢𝐝𝐞𝐧𝐜𝐞 𝐭𝐫𝐚𝐧𝐬𝐥𝐚𝐭𝐞𝐝 𝐢𝐧𝐭𝐨 𝐭𝐡𝐞 𝐫𝐞𝐬𝐭 𝐨𝐟 𝐦𝐲 𝐥𝐢𝐟𝐞. Which is why I want to share this playbook with you. I never thought I'd make it in sales. I never thought I'd be a VP of Sales before 30. I never thought I'd run the #1 sales podcast with my best friends Nick and Sean. And today, we're releasing our first book: 𝐂𝐨𝐥𝐝 𝐂𝐚𝐥𝐥𝐢𝐧𝐠 𝐒𝐮𝐜𝐤𝐬 (𝐀𝐧𝐝 𝐓𝐡𝐚𝐭'𝐬 𝐖𝐡𝐲 𝐈𝐭 𝐖𝐨𝐫𝐤𝐬) 𝐢𝐬 𝐚 𝐬𝐭𝐞𝐩-𝐛𝐲-𝐬𝐭𝐞𝐩 𝐠𝐮𝐢𝐝𝐞 𝐭𝐨 𝐜𝐚𝐥𝐥𝐢𝐧𝐠 𝐬𝐭𝐫𝐚𝐧𝐠𝐞𝐫𝐬 𝐢𝐧 𝐬𝐚𝐥𝐞𝐬. Sales changed my life. And I believe it can change yours too. 𝐓𝐡𝐚𝐭'𝐬 𝐰𝐡𝐲 𝐰𝐞'𝐫𝐞 𝐦𝐚𝐤𝐢𝐧𝐠 𝐭𝐡𝐞 𝐛𝐨𝐨𝐤 𝐨𝐧𝐥𝐲 $𝟏 𝐮𝐧𝐭𝐢𝐥 𝐅𝐫𝐢𝐝𝐚𝐲. (Get it on Amazon or anywhere you buy your books) The calls won't be always fun, but I promise you... Cold calling sucks, and that's why it works :) #sales
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Joe Caprio posted thisSelling to sales teams.. do you go top down or bottom up? -PLG to attract users and then uplevel your pitch to power? -or Prospect top down relationships while you sell to their team? It's always both. >If your product gives the boss a more accurate forecast, it likely means you remove the rep's administrative burden of creating their forecast. >If your product enters the rep's data for them, it likely gives the boss more/deeper visibility into the deals. Make sure you know your value for each stakeholder and you're spending time on the right topics for the right audience. ✌
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Joe Caprio shared thisThanks for having me on 30 Minutes to President's Club .. always a total pleasure to rap with you! 😎Joe Caprio shared thisOn this episode of 30MPC’s The Leadership Show, Glasswing Ventures' Joe Caprio reveals how to build pipeline by engaging your prospects the right way and leveraging new tools to stay ahead of your competition. Listen at the links below 👇
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Joe Caprio posted thisWhat's your best prompt engineering cheat sheet? 🤔
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Joe Caprio posted thisSeeing pitches for new ai-enabled sales tech is enthralling, but it also makes me question my ability to give clear instruction or lead people. The pitch ends with, “..so that’s how we’ll use ai to [prepare for meetings, communicate clearly, multi thread accounts, negotiate well, etc]” And I nod my head enthusiastically as I say “Wow! I’ve always told my reps they should do that, but they never really did.” and then I begin to question my ability to give clear instruction and lead people. 😬
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Joe Caprio reacted on thisJoe Caprio reacted on thisExtremely excited to announce I’ve joined Deleteme (joindeleteme.com) and I’m working up in Boston again! Been great seeing all the old haunts, and would love to reconnect with folks
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Joe Caprio reacted on thisJoe Caprio reacted on thisThe inaugural off-campus event for the Bentley University E-Hub was a great success. Thanks to all who have grown the E-Hub from just an idea to an incredibly successful program in just 2 years, and an extra special thanks to Joe Caprio and Glasswing Ventures for hosting this event. Lots of fantastic alumni last night! Thank you for joining us Edward Keefe Lillian Keefe James Arredondo Susan Lowe Mavis G. Alex Hardy Sandeep Purao Myvette Fernandez Hicks David Mintz Cody Aguirre Clearwater Doug Adams Janak Joshi Jim Kelliher Caitlin Elinson
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Joe Caprio liked thisJoe Caprio liked thisI’ve been connected with the E-Hub at Bentley University for a little while now, and this year I’m excited to be taking on a larger role helping to lead the alumni mentorship initiative, connecting student founders with alumni who can guide, challenge, and champion their ideas. If you’ve ever been curious about Entrepreneurship at Bentley and want to get involved (as a mentor, supporter, or simply someone who loves seeing Falcons build big things), join us this Thursday for: Discover the Bentley E-Hub: A Gateway to Innovation Glasswing Ventures, 275 Newbury Street, Boston 5:30–7:00 PM Thursday October 23, 2025 Register here: https://lnkd.in/e5MAitQ5 Hosted by Joe Caprio and Sandeep Purao, Trustee Professor and Director of Bentley’s Entrepreneurship Ecosystem Initiative. You’ll hear how Bentley is investing in innovation, meet some of our rising student entrepreneurs, and get a glimpse of what’s next for the E-Hub.Discover the Bentley E-Hub: A Gateway to InnovationDiscover the Bentley E-Hub: A Gateway to Innovation
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Education
Publications
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The 5 Keys Of B2B Sales Negotiation
InsightSquared
See publicationTo get better at negotiations and achieve more win-win’s, follow these 5 keys of B2B sales negotiations.
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The SaaS Discount Epidemic
InsightSquared
See publicationI guess at some point, the tech community decided that the price of software was 100% negotiable.
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The 5 Analytics Reports Every Startup Must Have
InsightSquared
See publicationShameless Plug - come get your free Apps!
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Tales From the Frontlines: Sales Mentors
InsightSquared
In sales, a mentor isn’t just a nice relationship to have; it’s a vital part of every sales rep’s skill development and career growth.
Other authors -
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Half-Truths And Gut Feelings: The Sales Pipeline Management Dilemma
InsightSquared
See publicationInexperienced, inside sales reps need advice on where to spend their time.
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Sales Reps 2.0: Replacing The Door-To-Door Model
Young Upstarts
See publicationGoodbye steak dinners..
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Evolving Sales Reps for the Sales 2.0 World
small biz daily
See publicationPersonalize, Consult, ROI
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A conversation about Sports and Sales Coaching
Insightsquared
Why great coaches don't have to be great players and how great players gravitate to their coaches.
Other authors -
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Stefan Sexl
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Dwight Delap
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When agents can talk directly to your apps through an MCP server, everything changes. Instead of a human jumping between Salesforce, Airtable, etc... an agent can do it autonomously: Summarize call transcripts for target accounts from Gong Pass those summaries to Inflection to create custom segments Draft a target account campaign based on these custom segments No brittle integrations. No copy-paste workflows. No “please log in and click this button.” The agent just acts — safely, deterministically, and across systems via multiple MCP servers.
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