Over the past year and a half, we’ve had dozens of conversations with revenue leaders who all sound…tired. 

Tired of too many tools.
Tired of jumping between systems.
Tired of tech that promised to help but only added more noise. 

One sales leader summed it up: “We’ve invested in a dozen different systems, but my reps are spending more time updating them than actually talking to customers.” 

And it’s only gotten worse with the surge of AI. 

What was supposed to be the great productivity unlock, has in practice, often made things worse: spammy automated but impersonal outreach, obviously robot interactions, and clearly AI-generated content. Teams turned to AI to chase scale. But what buyers still want, and what wins deals, continues to be genuine human connection. 

The catch is, of course, that delivering thoughtful, personalized experiences takes time. And time is the one thing frontline teams don’t have. 

The Problem: Too Much Tech, Not Enough Context 

Today’s RevTech stack is bloated. Rather than evolving as a cohesive ecosystem, every tool solves a small problem and together they explode into a constellation of disconnected point solutions:  

• Siloed data where valuable insights remain trapped across platforms 

• Inefficient workflows that demand constant context-switching 

• Broken visibility that fragments collaboration between sales, CS, and implementation 

The result? Frustration. Wasted time. Missed opportunities. 

Today, when every deal is harder to close and every touchpoint matters, the companies winning are the ones using technology to enable the human touch – not replace it. 

Enter AskElephant 

AskElephant isn’t another sales tool. It’s something new and better – an orchestration layer for the messy, human side of revenue work. 

Most sales tech obsesses over prospecting automation. AskElephant focuses on everything after that first touch: where relationships are built, trust is earned, and deals are actually won. 

What makes AskElephant special is the way it blends effortlessly into teams’ day-to-day. It doesn’t ask teams to change how they work. It plugs in quietly, pulls the right data from calendars, emails, CRMs, and transcripts and turns it into something useful. It doesn’t just support one workflow or one role, it becomes the central nervous system for all revenue-facing teams, flexing across use cases with surprising range. 

Two features stood out to us: 

• A contextual intelligence engine that becomes your team’s second brain. Surfacing everything from customer objections to past meeting notes to action items, it’s a living intelligence layer teams can query without digging through five different apps. 

• A no-code workflow builder that makes it easy to automate the stuff that drives success but takes up a lot of time: follow-ups, handoffs, meeting prep, and customize it for every team’s needs. It works with your existing tools, automates key actions, and adapts to your team’s exact needs requiring no engineering.  

 It’s simple on the surface. Deep under the hood. Teams using it say it feels less like a tool and more like a true partner.  

“AskElephant has been a game-changer for our productivity. It ensures consistent messaging across teams, reduces friction…helping us move faster.” 

The Lightbulb Moment 

When we first saw AskElephant in action, it was a meeting prep workflow: in seconds, it pulled together a full customer brief featuring notes, transcripts, objections, and next steps. The kind of prep that usually takes 30 minutes (or gets skipped entirely) was done automatically, accurately and effectively – in far less than 30 minutes.  

But that was just one recipe. 

As I dug deeper, it became clear that meeting prep was just the tip of the iceberg. Customer success teams were using it for onboarding flows. Implementation specialists were using it to drive handoffs. Sales managers were automating coaching workflows. Even product and security teams were jumping in just to better understand customers.  

What started as a sales tool was quietly becoming a company-wide layer for smarter, more coordinated work. 

It became clear to me that this wasn’t just solving a point problem, AskElephant was addressing a foundational gap across the revenue org. And customers weren’t just adopting it; they were expanding use of the platform at a pace unprecedented for a company so early in its journey. 

AskElephant has grown 100% quarter over quarter. Teams at companies like Redo, Disruptive Advertising, ELB Learning, and Pest Share use it to work faster, stay aligned, and reduce friction. 

As one customer put it, “AskElephant has been a game-changer for our productivity. It ensures consistent messaging across teams, reduces friction…helping us move faster.” 

Backing the Right Founder 

Woody Klemetson gets it. He’s the very embodiment of founder-market fit. He’s been in the trenches, leading revenue teams at companies like Divvy and felt the pain of broken workflows firsthand. He’s building for the people doing the work, not just the people buying the software. 

What else sets Woody apart is how deeply customer-centric he is. He doesn’t build in a vacuum, he listens, iterates, and obsesses over making each workflow actually useful. That empathy shows up in everything. It’s reflected in the product’s flexibility, its intuitive design, and the way it wins trust inside organizations. 

Why Now 

This is a market that’s exploding. Analysts expect the AI-driven sales and marketing tech space to grow from $58 billion this year to over $240 billion by 2030. At Jump, we believe the next generation of breakout companies won’t be narrow point tools, but intelligent platforms that drive alignment and action across the entire revenue org. 

• Companies want fewer tools that do more 

• AI is finally enhancing—not replacing—human workflows 

• Buyers expect higher-context, more thoughtful engagement 

• Revenue is increasingly cross-functional: sales, CS, and implementation moving as one 

AskElephant doesn’t just fit that thesis, it helps define it. 

We’re thrilled to lead AskElephant’s $6M seed round alongside High Alpha, Tandem, SaaS Ventures, and a crew of exceptional angels. We’re excited to partner with Woody and the team as they build the operating system for modern revenue teams, one that helps people spend less time wrangling systems, and more time building real relationships. 

Because the elephant in the room is this: revenue tech hasn’t been working. And AskElephant is finally doing something about it. 

Curious to see it in action? Get a demo of AskElephant and see how its helping revenue teams work faster, smarter, and more human. 

They’re also hiring! If you’re excited about building the future of AI-powered workflows, check out open roles here. 

This article is for informational purposes only and does not constitute investment advice. Jump Capital is an investor in AskElephant. Views expressed represent the opinions of the author and Jump Capital. Forward-looking statements involve risks and uncertainties, and references to specific companies and their capabilities do not constitute investment recommendations or guarantee future performance.