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In the new digital world brought about by the pandemic, sales enablement — the process of providing sales organizations with the information, content, and tools that help salespeople sell more efficiently — is incorporating AI and automation technologies. According to a 2018 Bigtincan survey, the majority of salespeople who use sales enablement software leverage automation or AI. Thirty percent of sales enablement users responding to the same survey believe that AI is having a positive impact on their strategy and tactics.

Gartner predicts that by 2020, 30% of all business-to-business companies will deploy AI to improve at least one of their core sales processes. The success of the growing collection of AI-powered sales enablement solutions is proof of this, with vendors like Gong landing hundreds of millions of dollars in venture capital investments. Highspot, a Seattle, Washington-based startup, is another well-performing player in the space, providing a suite of AI-powered sales tools including semantic search, in-context training, and guided selling to customers. After raising $200 million in February 2021, Highspot today announced that it closed a $248 million round at a $3.5 billion valuation, bringing the company’s total haul to $648 million.

AI-powered sales

CEO Robert Wahbe, a 16-year Microsoft veteran, launched Highspot in 2012 with former colleagues Oliver Sharp, David Wortendyke, and Scott Gellock. The four sought to develop a platform that could close the gap between sales strategy and execution, enabling organizations to create action plans for sales teams and measure what’s working with analytics.

Toward that end, Highspot’s Amazon Web Services-hosted tools leverage AI to generate playbooks as well as custom seller and buyer experiences. Algorithms analyze historical data, data sheets, marketing presentations, brochures, training videos, case studies, and other company materials for effectiveness, informing recommendations regarding ways the selling process might be optimized. Highspot also provides apps to streamline talks and closes with current and prospective clients, and dashboards that enable sellers to see how buyers might interact with sales content and walk them through guided experiences such as interactive sales plays.


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“Even before the onset of the pandemic, buyers were trending toward self-reliance with a plethora of resources at their fingertips, researching vendors on their own time and relying on salespeople as mere transaction facilitators,” Wahbe told VentureBeat via email. “The sudden shift to a remote business landscape caused by COVID-19 accelerated this trend, and now modern buyers prefer — and expect — fully virtual sales … A handful of sales tech companies anticipated the trend toward digital selling, and strategically designed their products to help turn salespeople from transaction helpers into heroes. Highspot is one such company.”

Highspot delivers insights about what content sales teams and team members are using, and the platform tracks modified content back to its original source so that engagement metrics aren’t lost. All the data feeds into custom reports for ongoing tracking.


Above: Highspot’s sales enablement dashboard, where users can track progress toward goals.

Image Credit: Highspot

Highspot recently launched new capabilities including the AI-driven Engagement Genomics, which auto-relates buyer engagement data to the appropriate customer relationship management record — taking the manual effort out of connecting sales outreach to customer relationship management records. The company also introduced Highspot Marketplace, an exchange where Highspot customers can tap marketing, sales, enablement, and customer success content from third-party partners.

Substantial expansion

Highspot has achieved impressive growth over the last few years, boosting revenue by 935% from 2019 to 2022. Wahbe says that DocuSign, General Motors, Nestle, and Verizon Media are among the over 700 customers using the platform — which now employs over 800 people — to manage content, train and coach sellers, and engage buyers.

“[Our] revenue grew 935% over the last three years, annual recurring revenue retention was greater than 130% over the last 12 months, [and] Highspot connected more than eight million salespeople, channel partners, services reps and customers in digital sales experiences last year — representing a 150% increase in platform usage from the previous year,” Wahbe added. “[This demonstrates that] Highspot [is improving] the performance of … customer-facing teams by helping companies create a scalable, repeatable revenue engine … In short, our software [is making] it easy to build, deliver, and analyze the impact of the content, sales plays, training, coaching, and customer engagement that are fundamental to any go-to-market strategy.”

Beyond enablement, enterprises have shown an acute interest in adopting (or increasing their usage of) AI-powered software to bolster sales performance within their organizations. According to a 2020 Statista survey, 79% of marketing and sales department witnessed revenue increases of 5% or more after using AI for tasks like pricing and prediction of likelihood to buy. And a Harvard Business Review study found that companies applying AI to sales were able to increase their leads by more than 50%, reduce call time by 60% to 70%, and realize cost reductions of 40% to 60%.

“Technologies that unlock human potential are foundational to our economic future,” B Capital’s Rashmi Gopinath, a Highspot investor, said in a statement. “Highspot’s undeniable performance, coupled with the enthusiasm of their customer base, is a testament to how transformative their technology is for companies across industries and geographies. We believe Highspot’s platform is an imperative for businesses aiming to drive sustainable growth.”

New investors B Capital and D1 Capital led Highspot’s latest round with participation from existing investors ICONIQ Growth, Madrona Venture Group, Salesforce Ventures, Sapphire Ventures, and Tiger Global Management. The company says it’ll use the funding to deepen investments across its business as it expands globally and “accelerates” product development.

[The] new funding will fuel the company’s long-term growth, enabling Highspot to aggressively invest in building its unified sales enablement platform, expanding internationally including recently-launched operations in France and Australia-New Zealand, and hiring across all business functions,” Wahbe continued. “Sharp, Wortendyke, and I founded Highspot with the mission of transforming the way millions of people work and, in 2021, more than 8 million people interacted with the Highspot platform in some way, as the company continues to make its aspirational mission a reality.”

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