FIRST COHORT LAUNCHES WEDNESDAY, MAY 28TH

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FIRST COHORT LAUNCHES WEDNESDAY, MAY 28TH |

FOUNDERS
SELLING
BENEFITS

A GTM + Sales Accelerator for Founders Who Need HR (+ Brokers) to Say Yes

Learn How to Really Break into Employer Deals & Broker Networks in 8 Weeks

Founders Selling Benefits is a GTM and Sales accelerator for startup founders selling to HR and employee benefits brokers.

Learn how to shorten your sales cycle, land enterprise deals, and scale revenue — without spinning your wheels.

First cohort launches May 28th, 2025. Spots are limited to 10 founders.

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PROVEN HR SALES & GTM STRATEGY

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SCALE YOUR EMPLOYER REVENUE

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BUILD A REPEATABLE SALES MOTION

YOU HAVE A GREAT PRODUCT.
HR JUST ISN’T BUYING IT (YET).

Selling into HR, employers, and broker networks isn’t like selling to consumers. The sales cycle is longer, decision-makers are risk-averse, and the buying process is layered.

If you’re:

❌ Struggling to get past the first call
❌ Hearing “this sounds great, but not right now”
❌ Unsure how to price, position, or close employer deals

… then you don’t need more cold emails of paid ads.

You need a repeatable system for turning HR interest into signed deals —faster.

That’s exactly what we’ll build—together.

STUCK IN THE SALES CYCLE?

IF THIS SOUNDS FAMILIAR — THE ANSWER IS YES.

→ You know HR & brokers could be a goldmine—but they’re impossible to sell to.

→ You’ve had interest from employers, but deals stall out or take forever.

→ You’ve landed a few HR contracts, but need a repeatable system to scale.

→ You’re tired of second-guessing your pricing, positioning, and outreach.

INTRODUCING

FOUNDERS SELLING BENEFITS

Instead of guessing your way through HR and broker sales, imagine having:

  • A clear, structured GTM roadmap designed for HR buyers.

  • Playbooks that turn interest into contracts—without endless follow-ups.

  • The exact outreach, messaging, and pricing strategies that work for employers.

  • A sales & marketing system you can actually scale.

That’s exactly what Founders Selling Benefits gives you.

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WHAT’S INSIDE FOUNDERS SELLING BENEFITS

This isn’t another generic sales course. Founders Selling Benefits is an 8-week accelerator designed to give you a clear, repeatable system for breaking into HR and broker deals—without spinning your wheels.

Each week, you’ll gain the exact strategies, playbooks, and sales motion to turn interest into signed contracts faster.

90-Minute Weekly Masterminds

Get live strategy guidance + direct feedback on your GTM execution.

A GTM Roadmap + 60-Day Action Plan

A done-for-you tailored 60-day plan for landing employer and broker deals.

Dedicated Slack Channel

Direct access to Diana and peer support from other founders.

HR + Broker Specific Sales Playbooks

Cold outreach templates, broker partnership strategies & positioning frameworks.

Live Broker and HR Q&A Session

Get direct feedback from actual HR leaders and employee benefits brokers.

Ongoing Alumni Slack Access

Stay connected and refine your GTM strategy even after the program.

STOP CHASING DEALS. START CLOSING THEM.

HR and brokers aren’t ignoring you because your product isn’t great. They’re ignoring you because your sales strategy doesn’t match how they buy.

Founders Selling Benefits gives you the exact GTM + sales playbook to:

  • Turn HR interest into signed contracts—faster.

  • Position your startup as a must-have (not just a “nice to have”).

  • Break into broker networks so they sell for you.

  • Create a repeatable system that works—again and again.This isn’t about working harder. It’s about working smarter with a system built for HR & brokers.

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MEET OUR FOUNDER

DIANA CARTER
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Diana Carter has spent nearly 15 years in sales and marketing within the employee benefits space, starting on the broker side before transitioning into growth marketing.

As the founder of Carter House Copy, she has helped startups selling to HR, employers, and brokers refine their GTM strategies, accelerate sales, and scale revenue. Through fractional CMO work, GTM consulting, and agency implementation, she works with founders to turn complex, slow-moving HR sales cycles into repeatable systems that close deals faster.

Her expertise helps startups:

  • Shorten HR sales cycles

  • Leverage brokers as a sales channel, instead of chasing every deal manually.

  • Position their solution as a must-have in employer benefits.

  • Land enterprise contracts and scale sales without burning out.

Founders Selling Benefits is the accelerator she wished more founders had access to—a structured, actionable playbook for getting HR and brokers to say yes faster.

Proud to move and shake with

Watch Diana’s 5-minute talk to HR leaders on why innovative benefits matter

BY THE END OF FOUNDERS SELLING BENEFITS,
YOU’LL HAVE

NO. 1

A Proven GTM System

Land employer and broker deals with a repeatable sales motion.

NO. 2

Faster Sales Cycles

Reduce HR deal timelines from 12+ months to 3-6 months.

NO. 3

Clear Positioning & Pricing

Make HR see your solution as a must-have, not a nice-to-have.

NO. 4

A 60-Day Action Plan

Know exactly what to do next with a custom roadmap.

NO. 5

Confidence in Your Sales Strategy

Stop second-guessing—start selling with a system that works.

NO. 6

Broker Sales Strategy

Turn brokers into a sales channel that works for you.

TAKE IT FROM THEM ⬇️

TAKE IT FROM THEM ⬇️

  • "We love working with Carter House Copy! Diana and her team brought impactful GTM strategy and created detailed implementation plans. I'm thrilled with the materials we created and look forward to working with the team again."

    - Abbey Donnell, Founder, Work&

  • “Working with Diana was a game-changer for NCHIP. She helped us refine our go-to-market strategy with a sharp understanding of the HR and benefits broker landscape — and crafted messaging that genuinely connected with our audience. Beyond the strategy, her team clarity, enthusiasm, and a proactive approach that propelled us forward quickly. If you're trying to break into the HR or broker space, you'd be lucky to have Diana in your corner.”

    - Wes Grigston, Benefits Broker, Gallagher

  • “Diana is the strategic mind every founder hopes to find. She took the vision for CARRY™ Consulting and built a brand, message, and marketing engine that not only reflects our mission — but drives real traction with the right audience. I trust her completely.”

    - Paula Faris, Founder, CARRY™ Consulting

  • "When you have Diana and the Carter House team in your corner they turn your ROI into a story, and your CAC into personal meet and greet with your customer. They not only know how to identify your brand but also how to give it a voice that transcends just the founder."

    - Trish Erwin Golderer, Co-Founder, Little One Nutrition

  • "As a broker, it's beneficial for me to bring these types of innovative solutions to the table — because it shows that I care about the organization, and that’s what builds longevity for a broker."

    - Alexandria Lang, Benefits Broker, OneDigital

WHAT’S INSIDE

This isn’t a course. It’s an 8-week accelerator designed to help you build, test, and refine a go-to-market and sales strategy that actually converts — so you can attract HR buyers, increase employer adoption, and close more deals, faster. You’ll get expert guidance, live coaching, and real-time feedback every step of the way. Here’s a look at what we’ll cover:

    • Understanding the HR buyer journey & decision-making process

    • Employer vs. broker vs. partnership models (choosing the right GTM motion)

    • The three biggest mistakes founders make when selling to HR

Week 1

    • Creating a real ICP (Ideal Customer Profile) for HR & employers

    • Pricing, positioning, and offer structure for employer adoption

    • Crafting a high-converting pitch that speaks HR’s language

Week 2

    • Choosing the right GTM motion (Direct, Broker, Marketplace, Channel Sales)

    • Mapping out your sales funnel and demand-gen playbook

    • Leveraging case studies, pilots, and testimonials to build trust

Week 3

    • How to get HR & brokers to come to you (creating demand vs. chasing sales)

    • Best marketing channels for HR & employer adoption

    • Tactical playbooks: LinkedIn, content marketing, paid acquisition, webinars, lead magnets

Week 4

    • Aligning marketing & sales for employer deals

    • How to measure GTM success (KPI tracking, MQLs, pipeline health)

    • Optimizing & automating the lead-to-sale process

Week 5

    • Ask real decision-makers what works (and what doesn’t)

    • Learn how brokers & HR leaders evaluate new solutions

    • Direct feedback on positioning, messaging & outreach

Week 6

      • Each founder receives a customized 60-day GTM plan

      • Marketing & sales roadmap for demand gen, employer traction, and broker strategy

      • Training on how to execute effectively

Week 7

    • Review & refine marketing + sales strategies

    • Final adjustments, launch strategy & accountability plan

    • Wrap-up, networking & post-program growth planning

Week 8

  • We kick off May 28th and meet live on Wednesdays via Zoom from 12–1:30 PM EDT for 8 weeks. All calls will be recorded.

  • The full price is $6,000. That includes 8 weeks of live coaching, a customized go-to-market and sales plan, a private Slack channel for ongoing support, and access to live Q&A with real HR leaders and buyers in Week 6.


    You’ll walk away with a refined strategy, real-time feedback, and a GTM plan built to convert.

  • Due to the live, limited-capacity nature of this accelerator, we don’t offer refunds. If you're unsure if it’s the right fit, let’s talk first.

  • We cap each cohort at 10 founders to keep things intimate, high-impact, and highly personalized.

FREQUENTLY ASKED QUESTIONS

  • This is built for B2B founders selling into HR or employee benefit decision-makers — especially those in early growth or post-preseed stages who need a GTM and sales engine that actually works.

    Many founders do also have a D2C play — but the focus of this cohort/accelerator is B2B selling to HR/benefits brokers.

  • No problem. The strategies you’ll build are tailored to your brand, your ICP, and your sales process. In fact, founders often find it helpful to see how others are approaching the same market from a different angle.

    If a direct competitor is already registered for the cohort, we will let you know.

  • All sessions are recorded and shared in our private hub within 24 hours. That said, live attendance is where the magic happens — so making every attempt to attend every week in real time is only to your benefit.

  • You’ll have access to a private Slack channel where you can ask questions, share updates, and get feedback between sessions — plus, live Q&A with HR leaders in Week 6.

    After the accelerator ends, you’ll also have the option to join our alumni Slack group for $200/month. It includes ongoing community access and a monthly live Zoom session for Q&A, hot seat coaching, and continued workshopping with other alumni.

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LET’S TALK INVESTMENT

ONE TIME FULL PAYMENT

$6,000
(First 5 founders get $500 off)

What’s included in your investment:

  • 8 weekly live coaching sessions (90 minutes each)
    Small-group strategy calls led by Diana Carter, Fractional CMO and GTM expert. Come with questions, leave with direction.

  • A customized go-to-market and sales plan
    Delivered in Week 7 and tailored to your audience, product, and growth stage—this becomes your roadmap post-program.

  • Private Slack channel (for your cohort only)
    Get direct feedback, share updates, and ask questions between sessions in a focused, founder-only space.

  • Live Q&A with HR buyers and brokers in Week 6
    Hear what’s working, what’s not, and what makes them say yes —straight from the source.

  • Templates, worksheets, and positioning frameworks
    Proven resources designed specifically for B2B startups selling into HR, People, and Benefits leaders.

  • Optional alumni community access
    After the program ends, continue the momentum by joining our alumni Slack group ($200/mo) with monthly Zoom sessions for live Q&A and strategy workshopping.

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