We're Back - RDSW Content Highlight and Learnings Plus the 2025 Tweener List!
The extended Tweener Times Spring Break is over and we're here to recap all the RDSW goodness.
Tweener Times readers, right after RDSW, I had Spring break and then due to some personal stuff had to take a bit more time, but I’m back and we have a huge backlog of content to get to, so the rest of April is going to be crazy, buckle up! 🚀
RDSW → Tweener Mania!
During RDSW, we cranked up the energy with a full lineup of Tweener-powered action. From really deep dives on GTM and Product at the Tweener Workshops, to celebrating local startups at the Tweener Awards ceremony, we left it all on field.
Thanks to everyone who showed up, supported, and brought the magic that makes our startup ecosystem so special.
Enjoying the content? Our content is supported by the community so we appreciate you subscribing now and we REALLY appreciate it if you go paid!
Before we get into the details, a quick word from our amazing sponsors!
ExtensisHR - As a Professional Employer Organization (PEO), ExtensisHR empowers tech founders and growing businesses to scale smarter. We take HR administration off your plate—managing payroll, recruiting, employee benefits and retirement plans, compliance, risk, and more—so you can focus on innovation. For over 25 years we’ve leveraged a people-first approach, customer-centric mindset, and deep industry expertise to ensure employers have the tools needed to stay competitive in today’s market.
Bank of America – BofA’s Transformative Technology Group helps game-changing tech businesses and founders realize their boldest ambitions across a wide range of technology sectors. With hands-on support, world-class resources, and an extensive network – BofA provides the stability and scalability that tech companies need to rapidly grow today and into the future.
Whitley Recruiting Partners - Whitley Recruiting Partners specializes in recruiting top tech talent for growth-stage startups in the Triangle. We target industry-specific, entrepreneurial employees who drive immediate results through a fast, accurate, and scalable recruiting process. Special offer for Tweener Times subscribers: Free survey of available local talent for one of your openings.
Aligned Technology Group - Navigating cloud costs as a startup? ATG helps you maximize AWS Activate credits—up to $100K for startups and $300K for AI-driven startup businesses. As an AWS Advanced Tier Partner, we streamline your cloud journey, optimizing security, scalability, and cost efficiency. Startups move fast. We help you build smarter. Let’s unlock your AWS credits today.
Robinson Bradshaw - A full-service business law firm with a passion for supporting the Triangle entrepreneurial ecosystem. Learn more about Robinson Bradshaw’s startups and venture capital practice here.
EisnerAmper (formerly HPG) - One of the world’s largest business consulting firms, with a dedicated technology practice offering outsourcing, accounting, tax, and advisory services. Our experienced professionals serve more than 2,000 technology companies, from early-stage startups to public enterprises. Discover how EisnerAmper’s stage-specific solutions and industry expertise can help you achieve your milestones whether startup, international expansion, M&A, or IPO: eisneramper.com/tech.
Triangle Tweener Workshops
At Raleigh-Durham Startup Week, Robbie and I hosted two interactive workshops for later-stage startup founders.
Workshop 1: Go-To-Market in a GenAI World
The first workshop, "GTM in an AI World," focused on the transformative impact of generative AI on go-to-market strategies. GTM experts offered insights on effective tactics such as Account-Based Marketing (ABM) and LinkedIn outreach.
Industry experts included:
Ryan Walsh - CEO, RepVue
Grayson Leverenz - Founder, Groove GTM
Mike Genstil - CEO/Co-founder, ValueCore
Karly Pavlinac - Founder, MoreCustomers
Parker Mayes - CEO, Inbound Revenue
Our Tweener Friend Rajiv Kaul at Intelligaia put together this Sketchnote for the GTM session that captures many of the highlights: (click to enlarge)
Who better to summarize the workshop then the speakers themselves?
Grayson Leveranz added her perspective:
Parker Mayes gave his opinions on what is important in GTM strategies:
and Karly Pavlinac added:
Some more takeaways:
Grayson highlighted:
Keep it human and integrated
“One message - many channels” is the goal of integrated marketing, and the theme of 2025 is connection-driven marketing.
Participate in events, both live and digital, and repurpose the content for your audience.
Go deep on ABM (account-based marketing) by identifying people in your ICP (ideal customer profile) and adding value before you start selling.
Frame it like you’re going back-to school
Include stats and quotes from experts.
Cite your sources to help the LLMs trust and prioritize your content.
Stay curious about the tools and the humans connected to them.
Mike called out→
Tools:
Use Fathom for call recording - review the MEDDICC summary to understand how the customer perceives the solution, propensity to buy, etc.
Zoominfo intent data (and other sources) can be helpful but you need a BDR to follow up and scrape possible contacts at companies with intent
(watch out) Zoominfo subscription model is hairy. Each person gets a certain number of use it or lose it credits per month; very hard to optimize for the company
Strategy:
Say something personal and based on operational/ financial value, based on publicly available data, or data you've scraped. Quantitative + qualitative helps. ValueCore can help here (can do complimentary workshop for Tweener firms for example).
Outbound should include some offer / high value consideration. Free work (personalized), review of their current practices, etc. Even an Amazon card can work - this has been offered to me and it's been effective.
Parker concluded:
Tools:
We're using Apify actors for LinkedIn intent data - things like post content, new jobs, job listings
Enrich Data using Apollo.io (emails and phone numbers)
Dripify.io for LinkedIn DM automation and sequences
Using Instantly.ai for email sending and automation
Front.com to auto-draft sales email replies, auto followups to sales calls, and client draft emails (through Zapier.com / trained ChatGPT models)
Quick notes:
If you're doing sales activities manually make sure you're GETTING CREDIT for it! Personal videos, deeper research, making something custom for them.
If you're not getting credit for doing it personally, figure out how to AUTOMATE it.
Especially in service based/tech enabled B2B businesses, a great offer is key to sales success. What would it look like for you to have a NO BRAINER offer? Build trust first with an UP FRONT offer to help, prove your expertise, and show how valuable working with you could be for them.
Here’s some pics from the GTM workshop:
Workshop 2: Accelerate Product Motion with AI + ShapeUP
The second workshop, "Accelerating Product Motion with AI and Shape Up," addressed the slowing pace of product development for startups in the $1-5 million annual revenue range, showcasing how AI tools and the Shape Up framework can enhance efficiency.
Product Building Experts in the workshop were:
Cameron Bowe - CTO, ReFiBuy
Ryan Eade, CTO, Spiffy
Jim Grundner - Head of Engineering, AllStacks
Here’s Rajiv’s take on these workshops with three Sketchnotes!
Ryan Eade provided a few key takeaways:
Cameron Bowe added:
Jim Grunder spoke on AI and Product Development:
Tweener Awards Recap: A Big Night for Startups
Every spring, we come together to celebrate the Triangle’s startup momentum—honoring standout accomplishments from the prior year and unveiling the new Tweener List.
In partnership with Raleigh-Durham Startup Week (RDSW), the 2025 Tweener Awards brought founders, investors, and ecosystem partners together for an unforgettable night at the Durham Bulls Athletic Park. With an open bar, good vibes, and the whole startup community in one place, it was the perfect way to celebrate what makes this region special.
We recognized:
6 Tweener Top Exit
10 Tweener Top Fundraising
1 Tweener Madness champion
And welcomed 39 new startups to the 2025 Tweener List
Want to meet the companies shaping our region’s future?
👉 Visit www.tweenerlist.com to see the full list and explore each new 2025 addition.
Thanks to everyone who joined us—it was Tweener Mania in the best possible way.
Super big shoutout to our own Rebecca Ross who worked tirelessly to deliver everything that had to happen to make RDSW ‘Tweener Day’ such a huge hit! 🎉
Thank you!! 🫵
RDSW reminded us what’s possible when a community shows up for each other. From bold ideas and breakout moments to the quiet conversations that spark the next big thing—it’s the people that make this place special.
To everyone who shared a stage, raised a glass, asked a question, or simply showed up: thank you. And to our sponsors and subscribers, we’re sincerely grateful.
The momentum is real. The bar is high. And the best part? There is more coming your way! Stay tuned true Triangle believers…