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.”

Groove – Seismic Integration

Selecting Seismic content for inclusion in a Groove email flow

Groove and Seismic announced an integration partnership to “deliver relevant, approved, [and] compliant” Seismic content and LiveSend links within the Groove Sales Engagement Platform.

“Personalization is no longer a nice-to-have, but rather is an expectation from customers in today’s digital-first B2B sales environment,” said Preseetha Pettigrew, Seismic Global Vice President, Strategic Alliances.  “This integration with Groove streamlines the seller workflow, allowing frontline teams to focus on nurturing relationships and deliver greater value to clients.  I look forward to seeing how our joint customers benefit from this partnership.”

The integration delivers relevant content and CRM data within the Groove workflow and assists with intelligent content discovery.

“In today’s increasingly digital and remote B2B sales environment, this integrated solution bridges a critical gap between the point of engagement and Salesforce that helps companies quickly realize time-to-value, without a heavy lift from their IT or application development teams.  And easing the transition to remote selling is critical. Gartner’s 2020 Future of Sales research projects that 80% of B2B sales interactions between suppliers and buyers will occur in digital channels.”

Groove Director of Communications Jason Klein

Speaking to their joint value proposition, Groove Director of Communications Jason Klein said the firms share a “customer-first approach” to engaging clients in a “customized, data-driven, and scalable way while maintaining high compliance standards.”

Seismic Spring Enhancements

Sales Enablement vendor Seismic rolled out a set of platform enhancements last month that are “designed to help organizations capture every revenue moment and drive effective, efficient buyer engagement across all digital channels.”  The release included Seismic Aura, their new AI Engine for sales content.

Seismic Aura employs AI and machine learning to surface “new business opportunities and increase seller efficacy.”

“Over the last year, we’ve witnessed an incredible shift to all-digital buyer engagements. At Seismic, we’ve anticipated this change for some time now.  Our platform exists to make go-to-market teams more effective, whether their buyers are face-to-face or remote,” said Chief Product Officer Krish Mantripragada.  “The next challenge for technology leaders like Seismic will be to enable businesses to thrive in this new era of digital-first selling.  The innovations we’re launching at [Seismic’s virtual conference] Shift, along with the product updates we have coming later this year, bring sales and marketing teams closer together, helping them reach new customers and engage with existing customers in a compelling manner regardless of where they are.”

Continued Mantripragada, “humans can analyze only so much. Buried inside data are patterns, behavior, and insights that will hold keys to your questions and undiscovered opportunities. We are combining human intelligence and machine intelligence to harness the power of this data.”

Other Spring 2021 release features include

  • CRM SmartPlays employ predictive intelligence to recommend the most effective sales plays at any moment.  SmartPlays are delivered within the rep’s CRM workflow.
  • Seismic Sidekick, a Chrome extension powered by Aura, delivers guided selling and content recommendations “based on past engagement, similar buyers, and interests specific to each contact.” Sidekick helps surface engagement opportunities and reduces time spent searching for content.
  • Dynamic Email Templates
  • Global Privacy Management supports GDPR and country-specific, multi-lingual privacy requirements and notifications.
  • Groove and Seismic announced an integration partnership to “deliver relevant, approved, [and] compliant” Seismic content and LiveSend links within the Groove Sales Engagement Platform. The integration delivers relevant content and CRM data within the Groove workflow and assists with intelligent content discovery.

Along with announcing new features, Seismic boasted about its ongoing momentum.  Their net retention rate stands at 111%.  They have over one million users at over 700 enterprise clients, including deep penetration in the financial services sector.  Seismic claims that 22 of the top 25 global asset management companies are customers, along with 7 of the top 10 US banks and 4 of the top 5 North American wealth management firms. Seismic added over 200 employees last year and opened its first Canadian office with the December Grapevine6 acquisition.  They now have more than 1000 workers across fifteen offices.


Continue to Groove – Seismic Integration.

ZoomInfo Workflows Enhanced (Part III)

Continuation from yesterday’s article about ZoomInfo Workflows (Part I).

ZoomInfo hinted at an even broader vision of automated lead qualification and workflows in a recent blog that listed four categories of qualifying data:

Source: ZoomInfo, “How To Automate Lead Qualification for Increased Response Rates,” March 8, 2021 Blog.

ZoomInfo does not support programmatic advertising, chatbots, or Slack notifications, so there is significant running room for product development, particularly around expanded intent.  For example, a recent study by XANT found that inbound lead response rates decay quickly, but reps fail to respond promptly, and many fall between the cracks.  The study analyzed three years of inbound leads at over 400 companies.  XANT looked at 5.7 million inbound leads and found that 57.1% of first call attempts took place after a week or more, and only 0.1% of inbound leads were responded to within five minutes.  However, firms that responded within those first five minutes had an 8X conversion rate versus later return calls.

“Maybe we simply didn’t realize what we were leaving on the table,” wrote XANT.  “Maybe we over-rotated on targeted ABM strategies at the expense of speed-to-lead.  Marketing automation shouldn’t replace meaningful and quick sales engagement.”

XANT proposes a second problem that slows lead response times: the manual assignment of leads to individuals, resulting in two sets of delays – the lead routing process and the sales reps’ ability to respond quickly when a batch of leads is handed to them.

Tying inbound leads (emails, webforms, chatbots) to workflows is the next step beyond enrichment.  It allows for immediate lead scoring, assignment, and routing decisions, speeding up the response rate while determining each lead’s best course of action.  The Trigger / Filter / Action methodology for intent and event-based leads fits perfectly with these other inputs.  Furthermore, Chatbots and FormComplete often gather a few extra qualifying details that would be filter inputs.

“There is perhaps no greater need than for sellers to be calling on the right people at the right time,” said SalesTech analyst Nancy Nardin.  “Fortunately, the level of accuracy and timeliness of data has improved by leaps and bounds with the emergence of AI, and improved data collection, cleansing, and enrichment.”

ZoomInfo Workflows Enhanced

ZoomInfo Workflows are natural language statements that follow a trigger/filter/action process.

ZoomInfo rolled out an upgraded Workflows product for automating trigger-based tasks.  The service sports a simplified natural-language UI for building workflows “in ways that feel conversational, simple, and secure.”

ZoomInfo Senior Product Director Apparao Karri explained that Workflows are at the intersection of go-to-market data availability and sales automation, calling it “the long tail of GTM automation.”

Continued Karri, “Intelligent Automation is a key differentiator for businesses, and the underlying technology stack is mature and ready to deliver at scale.  ZoomInfo Workflows is a product built on this framework to improve productivity, reduce lost opportunities, and bring consistency to the go-to-market motions.”

Product Marketing Director Thad Peterson contrasted Workflows with Marketing Automation Platforms:

“Marketing automation has existed for many years, but often on a generic playing field.  For example, when visitors fill out a form on a company website, marketers can drop their information into a sequence or a campaign in their CRM.  But those campaigns are limited because a form-fill mechanism doesn’t provide targeted and specific information for each of those prospective customers. Now we live in a world where individual sales reps can create hyper-targeted campaigns based on nearly every imaginable scenario.”

ZoomInfo Product Marketing Director Thad Peterson

The basic structure of a Workflow is triggers, filters, and actions.  Triggers are business events detected by ZoomInfo and include ZoomInfo WebSights (website visitor intelligence), technographic changes, Clickagy Streaming Intent, fundings, and ZoomInfo Scoops (e.g., projects, PPP funding).  Triggers may also be created from saved searches that identify new companies or contacts that meet the saved criteria.

Triggers act as signals subject to pre-defined filters.  The filters are conditions that must be met for an action to be taken.  They can be based upon ZoomInfo or Salesforce criteria.  For example, presence in an ABM list, meeting firmographic criteria, assigned to a rep in Salesforce, or not present in Salesforce.  Actions dictate the Workflow response and include sending emails, assigning contacts, creating records, or kicking off sales flows (cadences) in ZoomInfo Engage, SalesLoft, or Outreach.  Marketing actions can be processed through HubSpot, Pardot, Marketo, and Eloqua.

Actions include a processing frequency (e.g., daily, weekly) and limits on the number of exported records.  The limit works as a throttle so that reps are not overwhelmed with too many leads.  It also prevents a workflow from using up too many ZoomInfo credits.  Some actions have sub-actions associated with platforms (e.g. set campaign or cadence / sequence / flow).

Filters can also be employed for territory assignment, ensuring that the activity is routed to the proper sales rep.  As ZoomInfo has one of the deepest pools of professional contacts with emails and direct-dial phones, they can activate sales and marketing activity from anonymous account-level signals for targeted functions and levels.

“If businesses want to scale quickly, they can’t become mired in day-to-day tasks that can easily be automated,” said ZoomInfo CEO Henry Schuck.  “ZoomInfo’s Workflows eliminates redundant, repetitive tasks and helps teams to focus on the human side of closing business by establishing strong relationships with prospects and customers.”


Continue to Part II.

Groove Revenue Intelligence

Sales Engagement Platform Groove expanded its analytics with new revenue intelligence capabilities that support real-time opportunity and pipeline management and expanded ROI reporting.  The new capabilities support pipeline reviews with a single pane of glass workspace populated with real-time Salesforce data.

In its 2020 State of Sales Report, Salesforce stated that “High-performing sales teams are 1.5 times more likely to base forecasts on data-driven insights.” Ensuring that data is accurate, timely, and complete has long been an issue with CRMs, requiring sales reps to spend hours each week recording their activities and updating account, contact, lead, and opportunity data.

Sales Intelligence platforms have picked up the slack around CRM data, offering DaaS prospecting and enrichment services.  Likewise, SEPs capture most sales rep activity data, reducing activity tracking overhead; however, updating opportunity data and evaluating opportunity risk remain a significant automation gap.  

Maintaining Opportunity data, which is critical for pipeline reviews and forecasting, is made more difficult by the data structure of CRMs.  One common complaint about Salesforce is the difficulty of viewing and updating opportunity data, which is fragmented across accounts.  Revenue Intelligence tools from Clari, Revenue Grid, SalesLoft, and Groove simplify the data update and review process by providing a centralized interface for updating the pipeline and reviewing it with managers.  Updates are immediately written back to Salesforce, simplifying the pipeline management process and ensuring that current opportunity data is instantly synced in Salesforce.

While Clari and Revenue Grid focus on Revenue Intelligence, Groove and SalesLoft attack the issue from a Sales Engagement perspective.  This functional overlap between categories has been evident since SalesLoft acquired Costello in 2019 and integrated Costello’s revenue intelligence capabilities.  While Sales Engagement Platforms began as multi-channel messaging services for SDRs, they have significantly broadened their scope to include Analytics, Guided Selling, Engagement Metrics, Meeting Management, and Revenue Intelligence.

Anthony McPartin, Forrester Principal Analyst in Sales Operations, described the widening scope of these categories.  “This notion of the sales engagement platform as a cockpit for sellers is likely to continue to drive further integrations between other sales tech categories and these platforms as the advantages of bringing everything to the seller where they sell (the original vision for CRM technology) become more widely recognized.”

Revenue Intelligence Platforms have also expanded their scope, assisting with opportunity risk assessment, deal forecasting, conversational intelligence, and buying team discovery.

Out of date and incomplete information is a significant issue for B2B decision-makers.  According to a July 2020 Forrester study, two-thirds of B2B decision-makers are hampered by stale, distorted, or limited CRM data.

“From incomplete sales activity data to out-of-date information stored in shadow CRMs, there are many challenges that prevent sales organizations from trusting their pipeline and conducting comprehensive reviews. Today’s release solves a critical usability challenge that Salesforce users have faced since the platform’s inception, in a way that establishes transparency and trust between the rep and the seller.”

Groove CEO Chris Rothstein

“We had major issues with getting our sales teams to document what they were doing in Gmail, and this is where Groove really shines,” said Bart Johnson, Director of User Engagement & Training at Aquent. “Groove isn’t just a huge timer saver for our reps, it also gives them ‘cross-vision’ into the different orgs and groups selling into [each] account.”

SalesLoft Deal Engagement Scores

Sales Engagement vendor SalesLoft announced Deal Engagement scores, a “machine-learning capability [that] gives frontline managers an unbiased way to prioritize deals based on the calculation of over 30 data elements captured across Cadence, Conversations, and Deals.”

Instead of a black-boxed score, SalesLoft provides recommendations and an explanation of the score, helping sales managers identify opportunity issues and risks and take actions to improve close rates.  Thus, Deal Engagement Scores serve as early warning signs that deals may be going south, allowing them to take proactive actions that improve close rates.

Deal Engagement Scores are shown over time and include a set of stage progression indicators such as days since the last meeting, days until the next meeting, and close date pushes.  A seven-day summary details recent engagement activity and deal progression.

“It’s not enough to have just a Cadence product,” said Frank Dale, SalesLoft’s SVP of Product Development. “With Cadence, Conversations, and Deals on one platform, we collect data across the full buying cycle, from the first email, every call, meeting, and communication, through to deal closure and renewal.  Only SalesLoft can analyze all of this data to predict revenue outcomes.  No other Sales Engagement provider can offer this.”

SalesLoft published the 35 metrics that feed into their Deal Engagement Scores.

35 data elements are fed into their machine-learning model to prioritize and identify opportunity issues and risks. Engagement is measured across emails, phone calls, and meetings, with interactions measured by level.  Over 120 million customer interactions were fed into the machine-learning model. As a machine-learning capability, the model continues to improve and adapt. 

“Having this capability allows front-line sales managers an instant gut check on specific health for deals in flight,” posted CEO Kyle Porter on LinkedIn.

Deal Engagement Scores are available to early access customers with Deals functionality in the Enterprise and Sell plans.  It will GA by June.

Cognism Growth

UK Sales Intelligence vendor Cognism continues its rapid growth with $11.5 million in 2020 revenue.  CEO James Isilay anticipates 2021 revenue of $20 million.  ACV is around $14,000 with over 1,000 customers.

Cognism had an initial one-month hiccup due to COVID as customers in the recruitment and events space were hit hard, and the firm needed to transition to a WFH sales environment.  However, the firm is back to growing “and hitting its targets every month.”

“COVID helped us get way more efficient.  We didn’t need an office anymore, it slowed our headcount growth,” said Isilay.” We really have an engine now where we can just put more money into headcount in terms of SDRs or into marketing and then get more growth.  So it’s really just a question of how much we want to put the foot down on the pedal.”

Cognism CEO James Isilay

By the end of October, employment hit 179 with sixty headcount in Croatia and Macedonia.

When the firm acquired email signature marketing vendor Mailtastic back in May, they paid roughly $4 million for the company in a stock and cash deal.

Mailtastic’s net retention is around 110%, and the prospecting service is approaching 90%.  However, there is a high percentage of returning customers post-churn.  The company started in the SMB space and has moved up-market, so net retention should improve.

While the firm has a negative cash flow, it burns only $200K per month with six to seven million from the last raise sitting in the bank.  The August funding round valued the firm at a bit under $100 million.

Cognism offers sales intelligence, B2B DaaS, and sales engagement services. It maintains over 55 million European company profiles.

Groove Integrates with Sendoso

Sales Engagement Platform Groove announced an enhanced integration with Sending Platform Sendoso for enhanced email-based gifting.  The partnership lets joint customers send direct mail, personalized gifts, eGifts, and celebrity greetings to over 165 countries.  

The service helps revenue teams “strategically leverage gifting in their daily workflows to strengthen relationships, accelerate deal cycles, and re-engage dormant accounts,” blogged Groove Director of Communications Jason Klein.

Sales reps can send gifts from their email or send gifts after a meeting through Groove’s scheduler link.

“Unlike other sales engagement platforms that were built for prospecting, Groove seamlessly aligns with our AE and CSM workflows, making them more efficient and effective in their day-to-day workflows,” said Alex Miller, Sendoso Director of Revenue Operations.  “Our teams took to it right away, and we’ve subsequently seen 95% percent adoption across our sales and customer success teams. Not only are our reps more effective, but we have complete visibility into pre- and post-sales activities for every prospect, customer, and partner account in Salesforce.”

Sendoso claims that its customers see a:

  • 4X increase in response rates
  • 50% faster deal cycles
  • 20+ hours saved per campaign
  • 450% ROI on campaign investment

Sendoso recently ran a reactivation campaign with a 50% open rate and 21% conversion rate for booked meetings, resulting in a ten percent meeting book rate from within Groove Flows.  Reps are notified when gifts are delivered, helping raise conversion rates.

“Our AEs love that they can now live in Gmail instead of a separate app and still have Salesforce data at their fingertips and add contacts with a single click,” said Miller. “Whether an AE needs to jumpstart a stalled deal or a CSM needs to ensure a customer shows up for a meeting, Groove lets them easily send out a Sendoso-powered gift without ever leaving their workflow.”

Groove also has partnerships with Salesforce, MSD 365, Google Workspaces, Vidyard, Seismic, Highspot, and LinkedIn Sales Navigator.

XANT: Inbound Lead Response Rates

In March 2011, the Harvard Business Review published “The Short Life of Online Sales Leads,” which discovered that companies were slow to respond to sales leads, and there were considerable benefits from rapid responses.  The study is often cited, but there was little subsequent data to determine whether these issues and opportunities still held.  Fortunately, XANT recently replicated the study, looking at three years of inbound lead response and contact rates.

The new study analyzed 55 million sales activities at over 400 companies.  XANT looked at 5.7 million inbound leads and found that 57.1% of first call attempts took place after a week or more, and only 0.1% of inbound leads were responded to within five minutes.  However, firms that responded within those first five minutes had an 8X conversion rate versus later return calls.

“Maybe we simply didn’t realize what we were leaving on the table,” wrote XANT. “Maybe we over-rotated on targeted ABM strategies at the expense of speed-to-lead.  Marketing automation shouldn’t replace meaningful and quick sales engagement.”

XANT proposes a second problem that slows lead response times, the manual assignment of leads to individuals, resulting in two sets of delays – the lead routing process and the sales reps’ ability to respond quickly when a batch of leads is handed to them.

“Leads sit, go cold, and revenue slips,” warns XANT.

To address the slow response problem, XANT added a shared record option to their Sales Engagement Platform.  The goal is to work every lead with named accounts properly routed and other leads delivered to a shared pool with priority leads immediately offered to reps.   XANT provides AI tools and a rules-engine to auto-assign leads from target accounts and load others into a shared pool with prioritized leads labeled urgent.  The top-rated leads are then offered to the sales team on a round-robin basis, ensuring that all reps have access to top leads and that priority leads have rapid response rates.

“With records in a shared pool, reps won’t get bogged down or locked out,” said XANT. “High-performing reps can blow through their leads quickly and continuously draw from the shared pool.”

XANT describes Shared Leads as another robot that improves the efficacy of sales reps.

“Whereas many treat automation as a way to email spam, we treat it as an enhancement to improve engagement and sales,” explained XANT Head of Product Mark Littlefield. “The basics of Robots include auto-enrolling records, opportunity funnel progression, prioritizing tasks, triggering reps to customer events, performing reliable data entry, and a lot more.  With Shared Records, we’re bringing teams the flexibility to compile records into shared folders or automatically assign them to the right reps so they can accelerate their speed-to-lead and their time-to-value.”