The impact: AI-powered prospecting means more predictable pipeline for Jellyvision

Jellyvision is your partner in reinventing how employees choose and use benefits. Jellyvision technology delights and guides your people to make better benefits decisions — leading them, and you, to a more prosperous future.
Software Development
Chicago, Illinois, US

Learn how Jellyvision reps use to:

  • 4x pipeline generation
  • 3x prospecting activity levels
  • Improve rep ramp time

Jellyvision is no ordinary software company. With its unique and human brand voice, the firm has carved out a niche in the healthcare and HR technology sectors. But Jellyvision faced a classic conundrum in modern business: how do you scale outreach to hit lofty sales goals without diluting your brand's ethos?

Their solution: adopting, an advanced artificial intelligence (AI)-powered sales prospecting platform.

This case study captures the transformative journey of Jellyvision as it combines the power of humans and AI to scale go-to-market (GTM) operations.

A bit about Jellyvision

Jellyvision is a pioneer in the HR tech space, with a mission to simplify the complex world of employer-sponsored benefits and Medicare. Through its flagship product, ALEX, the company has assisted employees in making informed benefits choices since 2009. And it’s not just small-scale operations: Jellyvision caters to a diverse clientele, ranging from small firms to enterprise companies with millions of employees. Their recent acquisition of Picwell has supercharged ALEX’s recommendation engine, allowing them to leverage predictive analytics with behavioral science to provide better employee experiences.

Within the Jellyvision team itself, there were two leaders who played key roles in this story; as such, they'll be featured prominently throughout this case study:

  • Heather Green, enablement director
  • Max MacCready, director of sales

Jellyvision's challenges

Jellyvision's sales and business development teams needed to engage a vast pool of prospects to bring their current and new product lines to market. However, they also wanted to maintain their distinct brand voice — jargon-free, yet professional — in each communication.

"[We were] focusing on omni-channel prospecting efforts to target new and previously known accounts ... the marketing team would create the sequences based on best practices, but we would add layers of personalization to that. However, we found that our sales team struggled to sift through so much information to be able to actually personalize those emails ... and we weren't seeing a lot of success with it."

Heather Green

A range of challenges defined

  • Scaling activity, not headcount: Jellyvision was entering 2024 with ambitious business goals and needed a way to hit them that didn't rely on adding an unrealistic number of full-time hires.
  • Nuanced messaging: Each rep had a unique method for researching and personalizing emails when targeting HR professionals, who demand messages that are both engaging and meet industry standards. This led to a lack of consistency and efficiency, which — in turn — caused outreach volume to suffer.
  • Outreach velocity: Benefits enrollment season typically occurs between August and December, and Jellyvision needed to reach prospects more efficiently prior to this pivotal time of year.

Jellyvision sought out a partner that wouldn't just accelerate their outreach volume, but would also allow them to maintain the unique brand personality that sets them apart in a crowded marketplace. Furthermore, there was a cultural shift internally brewing toward embracing AI as a way to be more efficient with the team they have today.

"A big internal push was coming all the way up from our CEO to look at AI and the ways that it could create new efficiencies within our organization. So I was thinking: 'There's got to be something out there that effectively does what ChatGPT does but doesn't require me to become a pro prompt writer to be able to get the exact messaging that I'm trying to for.'"

Max MacCready

Choosing the right solution for the job: Why

In the fall of 2023, Max MacCready, who runs the account executive and BDR teams at Jellyvision, was doing strategic planning for the upcoming year. "Doing the back napkin math: this is my team's close rate, this is how many opportunities we are going to need, etc," explained Max. "To reach the level of activity and output we needed, I would have had to hire close to a team of 30 BDRs to support that. When I broke it down and showed the math to my CRO, it made all the sense."

Max decided then and there to rebuild his outbound prospecting motion using AI.

Before settling on, Jellyvision's leadership thoroughly explored various AI solutions to enhance organizational efficiency. Options like Apollo and Lead IQ were considered, but — ultimately — the team chose for its generative AI (genAI) native prospecting capabilities, integration into the sales workflow, easy implementation, and responsive team.

Jellyvision's three challenges, solved

From ICP definition up to meeting book, has streamlined the operational complexity of Jellyvision's prospecting motion and turned distinct parts of the outbound workflow over to AI.

1. Scaling activity, not headcount

Coming into 2024, Max revamped Jellyvision's sales territories and accounts strategy so that reps could work bigger books of business but use AI and automation to make the best use of their time.

For instance, Jellyvision uses Auto-Pilot Agents to autonomously prospect the thousands of Tier 2 accounts that reps have in their name. First, the Agents discover current gaps in their CRM; then, they search for ICP leads, dynamically sequence them, and warm up those leads with contextual, persona-based emails. For the prospects that demonstrate intent, the Agents serve up priority LinkedIn and call tasks for the reps to execute on — turning cold outbound into warm lead follow-up for the team.

"In years past, a BDR or AE would have to keep feeding themselves leads if they wanted to keep their prospecting engine going. Nowadays, the true motion when they start their day is going into Outreach, seeing what priority tasks are being lined up via Auto-Pilot, and completing those because they trust it's serving up good people to reach out to.
"The amount of time spent on the actual act of prospecting and then actually reaching out - limited our ability and reach to go to market. So by introducing Regie, we were able to significantly reduce the amount of time that teams are spending [on prospecting] and reapply it toward being able to reach out to that many more people per day."

Max MacCready

2. Nuanced messaging

Alternatively, Jellyvision reps take a much more strategic ABM-styled approach with their Tier 1 accounts. Each rep only has between 50-100 accounts, so for these, they use's Co-Pilot AI Assistant to help streamline the hyper-personalized email generation process for each prospect.

As a result, the amount of time it took reps to manually draft personalized emails decreased from 10 minutes to under two minutes in just two months.

Jellyvision simply wasn't able to maintain the volume and quality in prospecting to this degree before Regie. "If they're getting a message from us [Jellyvision], it's quality," explains Max. "That's because of the time and energy that myself and the customer success team at Regie have taken to make sure the [AI] is really sounding like what we'd otherwise expect our sellers to sound like."

3. Outreach velocity has also enabled Jellyvision reps to produce results more quickly to take advantage of the seasonality of their business.

"During the BDR ramp period, I can get accounts into the new BDR's names and get Auto-Pilot working them in the background, so by the time the BDR reaches the end of their 30-day ramp, they already have tasks served up for them by the Agent.
"I had a BDR who recently started, and by the end of his ramp, since I had Auto-Pilot working in the background, he set a meeting on Day 2 of being on the phones as a result of a call task generated by Auto-Pilot."

Max MacCready

Additional benefits

Thanks to this newfound capacity gain, reps largely reinvest their time savings from back into prospecting their highest-value Tier 1 accounts — specifically focusing on being that much more strategic with them.

They also invest their time savings back into other valuable work for the business.

"One of the big pillars that Jellyvision has tied themselves to this year in terms of company goals and culture is promoting this idea of a high-performance culture; being able to go outside of your role and have an impact on the greater organization.
"I have this one BDR on my team, Courtney, who is absolutely amazing. She, as a result of having more time back thanks to, had a chance to work with our sales enablement team to build out a Lessonly course that she was passionate about on buyer personas, behavioral science, and how to interact with individuals at different levels of their career.
"She could make an even larger contribution to the revenue organization thanks to the capacity gain from"

Max MacCready

The results

Jellyvision's primary prospecting challenges are now solved with, and it's driving tangible business results.

"A good majority of the pipeline we've been able to build this year is a result of tasks being served up by Auto-Pilot [Agents]," says Max. " is directly tied to revenue goals and is now inadvertently tied to some of the company goals that we have around high-performance culture."

Across their various Agents running, Jellyvision has scaled prospecting to thousands of future customers autonomously, yielding 40+ meetings and dozens of opportunities.

Due to the investments in — as well as opening up the calling channel — stats from the Jellyvision sales team comparing Q1 '23 to Q4 '24 performance include:

  • 4x more pipeline generated (i.e., $7.6mil vs $1.9mil - selling season of September to date)
  • 2.6x more initial demos held — an indicator of quality pipeline being worked (i.e., 40 vs 15)
  • Over 3x prospecting activities accomplished (despite lower headcount than 2023)
  • 81% to original full-year direct prospecting goal, whereas expected to be only at 66% to goal

The leaders behind the success

The two driving forces behind the rapid implementation and immediate success of at Jellyvision were Heather and Max. With constant support and guidance from their customer success manager (CSM), they achieved full-scale implementation across the sales force in an astonishing 30 days.

For their part, Max and Heather personify what describes as "Regie Role Models": individuals who aren't just active users but are also thought leaders who are continually evolving their strategies to remain competitive.

The takeaway: AI is a business game-changer not only streamlined Jellyvision's outreach process, but it also helped usher in this new age of modern sales powered by AI. By significantly reducing the time spent on list-building, prospect research, and message personalization, enhanced the efficiency of Jellyvision's sales and business development teams, reaching more prospects with a better experience in less time and driving hard ROI for the business. serves as a compelling case study on the transformative potential of AI when applied thoughtfully to a business.

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