MGMT Boston - W8, Q4 24 - 2025 AI Trends with Glasswing / Jenelle Kelly, SmarterX
2025 AI Trends with Glasswing / Jenelle Kelly, SmarterX / Vizit & BlueTrace on The Lantern
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TLDR:
2025 AI Trends with Glasswing VC - we broke out the crystal balls, red and green ones, to talk about 2025 predictions: AI as intern or CEO? / M&A ^ / More trust needed / Smaller teams / No 1 person unicorns
Thanks to Ali Mahmoud & Glasswing for hosting
Jenelle Kelly, VP of Customer Success at SmarterX - a masterful communicator & former broadcaster, post sales leader, and competitor who has turned a passion for helping people into building and leading customer facing functions
Thanks to Matt Haley for the intro
The Lantern Last Week: Jehan Hamedi, Vizit / Drew Condon, BlueTrace
Thanks to Nick Abate for the intro to Vizit and Matt Shapiro for the intro to BlueTrace
Other Resources:
MGMT Boston Operators Club - a community and opportunity engine for 90+ Boston based up & coming venture backed operators
2024 Boston Tech Big Board - 2024 Companies to Watch (evolving list)
NEW - Trusted Partners - top local partners I’ve worked directly with or would trust with my own resources
The Endeca Effect: Overview / Markets / People / Products / Conclusion / Bonus - Steve Papa Alumni Learnings
Q4 Startups Highlighted: Cyvl, Modulate, PredictAP, Clasp, Clockwork
Q4 Operators Highlighted: Laura Andre / Qunett, Dana Louie / InvoiceCloud, Sarah Clarkson / Vestmark, Brian Mongeau / Caveonix
2023 1H Recap / 2023 2H Recap / 2024 Q1 Recap / 2024 Q2 Recap / 2024 Q3 Recap
2025 AI Trends with Glasswing VC
Thank you to Ali Mahmoud, Elizabeth Hilfrank & the rest of the Glasswing team for hosting the MGMT Boston Operators Club last Thursday to talk about AI in 2025.
And thank you to Ries McQuillan from Baker Tilly for moderating our panel & sponsoring the event with two extremely talented builders in Adrianna Gugel (Chief Product Officer and Co-Founder @ Flux) and Sharon Roth (Senior Director Product Management @ Quantified.ai).
We broke out the crystal balls, red and green ones, to talk about what we thought was likely and unlikely to happen in 2025 when it comes to AI.
Ali and Glasswing are excited about AI-driven workflow automation. Adriana views 2025 as the evolution in AI from a “tool for analysis” to “the most amazing intern” next year. Sharon is excited about how AI can continue to help unlock human potential, enhancing the performance of teams in 2025. Here are some other takeaways..
AI is not a bubble
In 2025 (and beyond) the question is whether AI applications can operate at “intern” level or “CEO” level
AI is part of the solution, not the whole thing
Bigger companies are likely to acquire AI startups in 2025, particularly those who have struggled to build AI into their own platforms
Companies want employees using AI, so if you don’t you might have a problem keeping your job long term. Make it a strength!
Teams will be smaller but preserving unique creativity is essential. With AI alone, you’ll look like everyone else
One of the barriers to mass adoption is trust. Until the data is more unbiased, this will be a challenge
The most interesting modality for 2025? Sharon thinks video. Ali & Adriana went with voice.
And no, there will not be a 1 person unicorn company in 2025!
Jenelle Kelly, VP of Customer Success @ SmarterX
Jenelle Kelly is a masterful communicator & former broadcaster, post sales leader, and competitor who has turned a passion for helping people into building and leading customer facing functions who tell the stories of enterprises through her teams. Today she is the VP of Customer Success at SmarterX, a data company giving retailers and brands the data they need to sell regulated consumer products.
Jenelle was influenced by strong female role models, including her late grandmother, who exemplified elegance and determination. Her family emphasized hard work and empathy, qualities she values deeply. These early lessons have shaped her approach to leadership; she sets high standards for both her teams and herself, while building a culture of inclusivity and accountability, similar to the one her parents instilled in her.
Growing up playing team sports, winning and losing together is something she has sought in her career, looking to find trust and vulnerability with the teams she’s a part of.. In early stage companies there are similar competitive experiences without playbooks or maps. Sometimes you fail, but at least you have each other, through wins and losses.
Jenelle went to Syracuse University to study Broadcast Journalism & Economics. A professor encouraged her to pursue a career as a Broadcast journalist as she waffled back and forth whether it would be “worth it”. She decided to give it a shot because, after a couple years, she could always go do something else.
Her broadcast career began in Elmira, New York. Whether highlight reels of Jenelle’s local news reporting can be found on the Internet, I can neither confirm nor deny. Choosing broadcasting as her first career was one of the best career decisions Jenelle has made. She learned to listen, communicate, and tell stories. All invaluable skills.
Her work required her to walk up to strangers and establish relationships quickly when they were going through some of their hardest days. She’s never heard “no” more in her life! It’s a difficult job. You learn a lot of resilience working long hours and talking to people going through something traumatic. She had to stay professional and continue to move through it, day after day.
Her second best career decision was leaving broadcasting. After a couple years, she had the maturity to say this was not the professional path she wanted to pursue. Moving to a new city every couple years, coupled with the ongoing changes in the media landscape (like increased political polarization and the rise of digital media), gave her confidence this was the right choice.
Jenelle moved to Boston to pursue a career more aligned to her personal and professional interests. Instead of telling the news, she began pitching news stories at PR firm LaunchSquad right near HubSpot’s Kendall Square offices as “big data” became a buzzword.
She loved her role there, sitting next to incredibly smart people and working with really cool tech clients like Gazelle, Level Up/Scavenger, Runkeeper, and more. Over 3 years at the agency, she got exposure to working at a startup sized company with a lot of responsibility.
Through some colleagues, she was eventually connected to Mavrck. They were building an emerging influencer marketing platform and hiring their first Customer Success Managers. Jenelle joined their team to handle client management but also take on responsibility for the full post-sales experience, including retention & renewals. The world of “post sales” really brought all of her professional skills together.
Mavrck originally ran influencer campaigns on Twitter and Facebook. They even made a push into emerging social media app Instagram. Ever heard of it? Her dad used to ask her what she did and his eyes would glaze over. Now he buys all of his clothes on IG! Mavrck was an early mover in the influencer marketing space and it was pivotal to be a part a period of rapid growth and personal autonomy.
As Mavrck grew, Jenelle’s responsibilities grew to oversee Customer Success, Onboarding and Implementation, Customer Support, and ownership of their renewal & post sales motions. She even hired 8 team members in less than a year, figuring out how things work on the revenue side of the house and the interactions between customers and the business.
Next, Jenelle wanted to challenge herself to experience Customer Success at scale and joined leading Boston cybersecurity & SaaS company Rapid7. They were a well established business but Customer Success was a maturing internal function. As an Enterprise Customer Success Manager, Jenelle managed a much larger book of business. She had to level up how she communicated and interacted with very experienced executives at F500 companies.
Most of all, she learned through the experience that she really loves working with early stage companies, leading people, and earning wins together as a scrappy team. So she took a role at rapidly growing startup Vendr, leveraging her learnings from Mavrck and Rapid7 to build out a structure and scalable process as they grew the startup & global Customer Success team.
Jenelle helped mature their Customer Success function, standardized processes and reporting to improve revenue forecasting, and led a project to migrate the revenue team into Salesforce. They even got to 99% forecast accuracy one quarter while enhancing what the customer journey looked like. During her tenure, the team grew globally to 25, and increased their multi-year contract footprint. At Vendr, Jenelle got exposure to navigating an acquisition and integration of another company.
Then Jenelle was recruited by a former colleague to join SmarterX. They are on a mission to help clients make more compliant and sustainable decisions about consumer chemical products like cleaners, cosmetics, batteries, and electronics. Along with helping divert waste to help the planet, she is building another high-performing global Customer Success & post sales team of 20.
Her responsibilities include owning the customer experience and all revenue, from new logo acquisition, to expansion and retention metrics. This is her first role reporting into the CEO; with that responsibility comes board exposure and having to navigate helping teams on the ground floor, while maintaining the 10,000 foot view.
Clear Communication
To be fair, I did go to college to be a professional communicator, but my communication skills have carried me in my career. I champion a direct and clear communication style, where I try to always lead with empathy. I’ve found a “pyramid” approach to communication works well in both a team setting and for executive communication. What I mean by that is to start at the top of the pyramid – clearly articulate the core message and most critical information upfront. Then, layer in detailed context and supporting data as needed. This strategy not only facilitates efficient decision-making but instills confidence that you’re fluent in the subject matter and can go deeper as needed. When communicating, I also like to “hit all the bases” – so I like to talk through critical topics live and then follow up in writing. Remember reiteration is important as it highlights key points and ensures comprehension across all levels.
3 Career Insights / Learnings
Embrace Change - The ability to embrace change has been crucial to my growth. I believe that action always trumps inaction because waiting for perfect conditions often means missing out on important opportunities. This approach also means making the best possible decisions with the information you have at the moment and understanding that progress comes through taking risks. When faced with challenges that push me outside my comfort zone, I see them as opportunities for growth and learning.
You Are Your Best Advocate - Throughout my career, I’ve taken to heart the advice that you must be your strongest advocate. While mentors and champions are invaluable in providing guidance and opening doors, it’s equally important to step up and make yourself heard. That often means raising your hand, taking initiative, and asking for what you need. It also means backing up your requests with solid data to build trust and credibility.
Perspective Is Earned - Perspective comes from experience and reflection—it’s something we build over time. I remind myself of this daily, using it as a guide to stay open to change and to advocate effectively. This perspective ties together everything else: it enables me to see the bigger picture, empathize with others’ points of view, and make well-informed decisions.
Jenelle plans to continue navigating being a working parent and leading and building early stage teams to scale and, ultimately, become an executive leader. Maybe even one day a CEO, having an impact on teams and hopefully making the world a better place. She’s well on her way!
If you want to learn more about Jenelle you can find her spending time with her active family, building GTM teams at SmarterX, or on LinkedIn. Thanks for communicating all of your experience and learnings! We’re excited to see the teams and people you lead to scale here in Boston in the coming years!
The Lantern: Jehan Hamedi, Vizit / Drew Condon, BlueTrace
Last week on The Lantern..
Jehan Hamedi, Vizit’s Founder & CEO comes on The Lantern to share what’s happening inside of Vizit after announcing their $25M Series B fundraise - adding team members, building an automated path to customer value, and leading with customer centricity:
Drew Condon & BlueTrace are automating the seafood supply chain, helping 500+ seafood businesses manage their inventory and grow. The team is looking for a seasoned Sales Leader to join them and they take full advantage of a tight customer feedback loop by co-locating above them at The Boston Fish Pier:
The Lantern - a short form video series by MGMT Boston featuring the best startups (+founders), ecosystem leaders, and ferociously talented operators in Boston
W11: Jehan Hamedi, Vizit / Drew Condon, BlueTrace
W10: Madeleine Smith, Civic Roundtable / Dana Wensberg, Paperless Parts
W9: Andrew Lau, Jellyfish / Will Lehmann, Step Function Ventures
W8: Palash Soni, Goldcast / Andy Palmer, Entrepreneur & Investor / The Market is Getting Better
W7: Daniel Pelaez, Cyvl / Sean Smith, Denim
W6: Jenni Goodman, Underscore / Jason Lavender, Electives / Productize Yourself
W5: Simon Taylor, HYCU / Nathan Rosenberg & Marc Printz, Farmblox
W4: Remen Okoruwa, Propexo / Amelia Van Camp, Mirakl
W3: Alex Ewing, OneScreen / Jess Lynch, FoundersEdge / What is MGMT Boston? And Why?
W2: Aniketh Mohanty, Wayfair / Amber Nigam, Basys.ai / W2 Summary (The Agents are Coming)
W1: Trailer Launch / Markit AI / W1 Summary (Setting the Culture)
Any feedback for me? One thing you liked? One thing you didn’t? Local startups or operators to highlight? Just reply to this e-mail!
See you next week!
-Matt