SalesLoft Hits $100M ARR (Part II)

(Continued from Part I) SalesLoft also announced that Calendly’s founder and CEO Tope Awotona joined SalesLoft’s Board of Directors.  Both RevTech firms are based in Atlanta.  Porter and Awotona met seven years ago at Atlanta Tech Village.

“It was clear from day one [that] he was an incredible leader who had a clear vision harnessed around delivering delightful customer experiences,” posted Porter on LinkedIn.  “Most of us know the success of Calendly and have learned of Tope‘s fascinating story.  We’re stoked to partner together and grow from his strategic wisdom, leadership learnings, and product-focused excellence.  Our ultimate goal together is helping our current and future customers deliver revenue excellence at scale.”

Salesloft Calendaring Functionality

Porter and Awotona discussed potential conflicts of interest, but those concerns were laid aside.  While SalesLoft has calendaring features similar to Calendly, SalesLoft maintains an open architecture and partner ecosystem with Calendly as a partner.

Porter echoed a recent Gartner observation that SalesTech is in a period of “mayhem” where customers are looking to consolidate their revenue platforms to simplify workflows and operations.  Porter sees SalesLoft as being at the vanguard of this preference for broad, open platforms.

“There’s been massive trends towards digital selling that have taken place,” said Porter.  “And then there’s another trend that we’ve seen emerge, which is companies have been using so many different revenue tools, but they really want to consolidate on a very few that they love, and that’s where SalesLoft comes in.”


Continue to Part III which discusses Porter’s long-term plans for SalesLoft.

Chili Piper and Calendly Funding Rounds

Meeting Automation vendor Chili Piper closed on its $33 million “Series Spicy” led by Tiger Global with participation from existing investors Base10 Partners and Gradient Ventures, Google’s AI-focused venture capital fund.  The Series B raised total funding to $54.4 million, most of which was raised over the last nine months.

The additional funds will be used to accelerate product development and global expansion.  The round will also help them build out its sales, marketing, and customer success teams.

“We’re excited to partner with Tiger Global, one of the most successful and prolific software investors in the world,” said Chili Piper CEO Nicolas Vandenberghe. “With hundreds of customers and tens of thousands of reps using Chili Piper adding spice to their calendaring efforts daily, we thought, why not raise $33 million to ensure we up our Scoville game?”

Chili Piper Funding (Source: Crunchbase)

Like many SalesTech companies, Chili Piper enjoyed pandemic tailwinds as businesses went remote and looked to streamline their calendaring.

“We’re proud to have so many customers scheduling meetings and optimizing their calendars with Chili Piper’s Instant Booker.  We know some people can’t handle how hot our platform is, but believe me, once you use software as pungent as this, you’ll never go back,” said CPO Alina Vandenberghe.

Chili Piper positions itself as a Meeting Lifecycle Automation company.  Beyond booking meetings, it handles inbound meeting requests, sets up follow-up conversations, and maximizes the value of meetings.  Meeting workflow features include setting and sharing agendas, booking next steps, logging notes and follow-up actions, and syncing with the CRM.

“Before we launched our inbound solution, Concierge, every company had accepted the industry standard 40% conversion rate on inbound demo requests — meaning that 60 out of every 100 inbound meeting requests (aka inbound leads) never converted into a held meeting.  The biggest culprit was speed to lead.  The moment a prospect submits a meeting request form on your website, you should be connecting to get a meeting on their calendar.”

Chili Piper Website, “What is Meeting Lifecycle Automation?

Chili Piper, founded in 2016, has 101 employees across 22 countries.  The company is structured as a fully remote organization.

Customers include Gong, Spotify, Intuit, Twilio, and Airbnb. Expect more spicy pepper puns in the coming months.

Chili Piper isn’t the only Meeting Management vendor to be gaining attention from the VCs. In January, Calendly closed on a $350 million Series B with OpenView Venture Partners and Iqoniq Capital.  The funding round valued the Atlanta-based scheduling firm at greater than $3 billion.  Last year, it doubled its subscription revenue to $70 million and grew its user base to ten million.  

Calendly has been profitable since 2016.  Nigerian immigrant Tope Awotona founded Calendly after a series of failed businesses.

The funds will be used to provide liquidity for early shareholders and employees.  It will also fund ongoing product innovation, including expanded appointment setting enhancements and integrations.  The firm plans to double its headcount (at 200 in January) and continue to build out its R&D operations in Kyiv.

As a freemium service, users can test out Calendly and license the service for either $8 or $12 per month.  The service is generalized, supporting business people, teachers, contractors, and freelancers.  It offers integrations with calendars (e.g. Outlook, Exchange, Google Calendar), video conferencing (e.g. Zoom, Teams, GoToMeeting, JoinMe), and payment services (PayPal, Stripe).  Calendly offers apps for Android, iOS, Outlook, Chrome, and Firefox.

“We really see ourselves as a leading orchestration platform,” explained Awotona.  “What that means is that we really want to remain extensible and flexible.  We want our users to bring their own best-in-class products.  We think about this in an agnostic way.”

“Calendly has a vision increasingly to be a central part of the meeting life cycle,” said Blake Bartlett, a partner at Openview. “What happens before, during, and after the meeting.  Historically, the obvious was before the meeting, but now it’s looking at integrations, automations, and other things so that it all magically happens.  But moving into the rest of the lifecycle is a lot of opportunity but also many players.”