Why We Invested in AskElephant

Businesses that will win in the post AI world will do so with the same formula used by winners from previous technology waves. Woody and the team at AskElephant are building this company, and we are thrilled to support them on their journey.

5.20.25
Article by
Mike Fitzgerald

The first time I met Woody Klemetson was on a Thursday night in his office. I was in Salt Lake City for other meetings and drove out to see him at the end of the day. After a string of texts, it was clear I had mixed up the date. He thought I was coming the next day....and I was standing in his lobby.  

No big deal. Woody invited me in, showed me to a conference room and we started talking. We both shared our backgrounds and then went deep discussing his consulting work that ultimately led to starting AskElephant

That initial conversation helped build the strong conviction we gained to invest in AskElephant. The founding story, the practical use of the product...all backed up by stellar customer references. This is a great fit for High Alpha, and we are thrilled to invest alongside our friends at Jump Capital, Tandem, SaaS Ventures, and more.  

Like many good software businesses, the software did not come first. Woody met with his consulting clients, understood what they needed and went about structuring his engagements with a blend of proven sales tactics and what is now possible with AI. He was helping his clients find customers and win business with a practical blend of experience and tools. His approach was not 'all AI, all the time'.

This was a really important insight for me. How do we bring the power of AI into jobs that need to be done today? Selling, for example. How does AI help a business development rep better prepare for a new meeting? How does AI create effective follow up communication for an account executive? Might AI take over these roles altogether? Sure, that could happen in the future. I wouldn't bet against it. But what will happen before jobs are eliminated is that many jobs will be enhanced by AI, and people will be more productive.  

The math is pretty simple. If a customer-facing employee can get more done in less time, they can increase their productivity. They can sell more by using AI to do certain tasks. This struck me as a practical use of AI, one that could be absorbed and used by a large swath of customers.  

AskElephant's AI powered platform automates workflows for customer-facing teams. It is a simple, yet very powerful, AI use case. And, importantly, the market is ready for AskElephant's solution. This is not a solution limited to big companies with AI support teams. In fact, many of AskElephant's customers are mid-sized companies who simply see the value in using AI to make jobs easier for their teams. Simple.  

I've read about and met with companies with much more extreme goals for AI. The demos are generally quite good and I enjoy seeing the art of the possible. I wonder out loud how ready the market is for this technology. What has to be true at a business to adopt a solution with advanced use of AI? In many cases, companies are ready for a demo, ready to be educated about what is possible. But are they ready to use precious budget on these solutions? Often, they are not.  

For the software company selling these advanced solutions, time becomes a factor. Can a software business with an advanced AI use case hold on for months or years until the market is ready for their solution? How long can this software business rely on early adopters, a thin segment of the market, to fuel their growth?  

There was a simplicity in our customer calls and market checks prior to investing in AskElephant. We talked to sales leaders who simply explained the value of their team members getting more done in less time.  AskElephant was a single pane of glass that integrated the next best action workflows. Satisfaction was high, as were the referrals to other, customer-facing teams within the business. We saw the potential for growth in every direction.  

Perhaps the best part of my visit with Woody came as we wrapped up, around 7pm. The small office was bustling with 12 or 15 people. Woody explained that several customers had come over to eat hot dogs and show off the workflows they had built in the Ask Elephant tool. A low key, high impact way for customers to get attention directly from the AskElephant team.....and the team to get a first hand look at their AI powered tools in action. Wieners and workflows.  

Businesses that will win in the post AI world will do so with the same formula used by winners from previous technology waves. They will balance a progressive application of technology with serving customers who are ready to absorb a solution that improves their business. Woody and the team at AskElephant are building this company, and we are thrilled to be along for the ride.

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