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.”

Exceed.AI Seed Round for AI Lead Conversions

AI Lead Conversion start-up Exceed.AI closed on a $4 million seed round led by Glilot Capital and West Fountain Global Fund.  Also participating were Alex Pinchev, former President of Red Hat, and Gur Shomron, the chairman of Israel’s WalkMe.  Funds will be deployed to expand into new markets and onboard additional marketing clients.

Exceed.AI pulls lead information from Marketo, Eloqua, HubSpot, Pardot, Salesforce, and SugarCRM to assist with conversations.  Features include an AI chatbot, SMS chatbot, email response bot, CRM synchronization, and an automated meeting scheduler.  Exceed also offers rules-based lead qualification and the ability to respond to questions.  Exception handling features include out-of-office follow up and no-show follow up.

“Some of our clients have seen up to a 39.5% increase in qualified leads for the same marketing efforts they already undertake without additional headcount,” said CEO Ilan Kasan. “Our strength lies in our multi-channel approach.  We reach audiences where crucial conversations occur when marketing teams are qualifying their leads.”

Exceed research found that out of office follow up results in a fifty percent lift in lead qualification.  They recommend a “short, cheery” welcome back email two days after the lead returns to the office before resuming the previous drip campaign.

“In a perfect world, every lead gets engaged by a human, but human follow-up isn’t scalable, and sales reps give up on leads too quickly,” said the firm. “So the majority of your leads are left untouched and sales opportunities are missed.”

Exceed noted that 44% of reps give up after one or two touches, leaving many leads to go fallow.  Bots will continue the touches, waiting for engagement.

“Robots are very good at speed, working at scale, they never get tired, they never complain, they’re persistent and they can process huge amounts of information,” Kasan explained to Entrepreneur. “Humans are good at relationships, feeling empathy. They’re very good at understanding nuance in complex situations.  Everything the robots are good at, humans hate doing and actually are not that good at doing.  And everything that humans know to do, robots don’t know to do.  This in essence is a partnership whereby the robot will automate all the manual repetitive tasks so the humans can focus on doing what they know to do best, which is closing deals, having conversations and having relationships.”

Sales reps should focus on tasks that require “critical thinking and evaluation,” blogged Head of Marketing, Billy Attar.  Conversely, “all tasks that can be handled by automation should be automated.”

“As a Sales Manager, you need to maximize the time your reps spend on tasks that require real human insight – the insight only they are qualified to give, ultimately representing the value they bring to the company.  Those human insights include researching prospects and evaluating each leads’ needs, interests and objections, answering their asked and unstated questions… all the things that Sales Reps and SDRs are supposed to do.”

Exceed.AI Head of Marketing Billy Attar

Exceed.AI lists Demandbase, SugarCRM, Hearst, The YMCA, and Universal Robots as clients.  Exceed.AI is located in Israel and Sunnyvale, CA.

Monthly pricing starts at $1,500 for 20,000 leads and unlimited use cases (campaigns).

Revenue Grid Guided Selling (Part II)

Continuing from Part I, a discussion of Revenue Grid and its approach to Guided Selling.


Revenue Grid looks to take the CRM system of record and supplement it with insights and actions that move deals forward.  Insights are both positive and negative.  Risk flags include “The decision-maker is not invited to the demo,” “Close data has been changed for the Nth time,” and “Pricing was discussed at the meeting, but no quote has been sent.” By delivering insights to sales reps and their managers, loose ends, which could result in deal losses or delays, are flagged.  Sales reps and managers can then act upon these insights.  Revenue Grid can also make suggestions based upon internal playbooks and best practices.

In short, AI, historical data, and real-time data are employed to build a set of insights and recommended actions.

Revenue Grid goes beyond engagement metrics at accounts. It delivers a broad set of insights that include competitor mentions, lack of recent decision-makers responses, meetings without agendas, quarterly and monthly trends, and team performance.  In January, sentiment analysis will be added to their insights.

An Opportunities view provides real-time pipeline visibility across all accounts.  Reps can quickly update any opportunity information with the updates synced with the CRM.  Sales reps and managers then have a single-pane of glass displaying current opportunities.  Managers are notified of deal size changes, close dates, and scores and can track activity flow.

The Opportunities view includes signals, next steps, last touch, and overview data, providing a quick synopsis of where each deal stands.

Conversational Intelligence records and transcribes voice and video calls, then indexes and analyzes meetings for insights.  Corporate email communications are also analyzed for insights.  Revenue teams and managers can review call transcripts and listen or view significant moments during the call, with summary topics and insights called out.  Conversational Intelligence is also available for coaching and onboarding sales reps.

Conversational Intelligence recordings and transcripts are saved to accounts and opportunities.

A meeting scheduler fronts Conversational Intelligence.  Reps can insert multiple time slots with clickable times in their emails or offer a calendaring link.  Events are automatically synced between Salesforce and Outlook or Gmail.  Other features include calendar delegation (i.e., setting up an admin or CSR to schedule meetings), recurring event scheduling, and group calendaring across the organization.

Salesforce email synching captures emails, scheduled meetings, contacts, tasks, and attachments.  Accounts, Contacts, Opportunities, and Custom Objects are available for syncing, and multiple records may be updated.  Salesforce admins can set up activity auto-log rules, triggering Salesforce processes.

Sales Coaching offers a team performance view that displays revenue booked by reps alongside leads processed and time spent on external meetings, inbound external meetings, and outbound emails.

A Forecasting report evaluates the target, best case, and committed revenue for the team with plan, commit, and open pipeline values for each rep.  Managers can also compare past periods to find trends and set triggers to send notifications when thresholds are exceeded.

An Activity view displays inbound and outbound communications from sales and marketing over time with adjustable time windows.  Unfortunately, the activity graph does not rescale, making it difficult to view activity over an extended period.

Revenue Grid also supports Relationship Intelligence, showing an Account relationship map and flagging individuals in the organization with established relationships for introductions or briefings.

Revenue Grid’s sales engagement features include multi-channel sequences, email templates, and email tracking.  Channels include email, phone, SMS, and LinkedIn.  Sequences may be managed directly from within Salesforce, Outlook, or Gmail.  All Revenue Grid capabilities are available in the native Salesforce mobile app, including email analytics, notifications, and sequences.

Admins can perform A/B testing of sequences.

Revenue Grid detects replies from one or multiple recipients, out of office notices, opt-outs, and bounces.  It then pauses or halts sequences automatically.  It even halts sequences if the recipient is mentioned in an email or meeting invitation.

An email sidebar displays Salesforce data directly within inboxes and suggests relevant, actionable Signals.


Continue to Part III.

Revenue Grid Guided Selling

Revenue Grid which describes itself as a Guided Selling vendor, offers a hybrid platform with sales engagement, revenue intelligence, relationship intelligence, meeting management, and conversation intelligence.  Unlike many startups in these spaces, Revenue Grid comes to market with fifteen years of experience building native platform integrations behind the firewall and in the cloud.  It then layers on top reports, analytics, and an Outlook/Gmail/LinkedIn sidebar for identifying opportunities at risk, next steps and missed actions, engagement scores, and pipeline analytics.

“Algorithmic guided selling leverages emerging AI technology and existing sales data to guide sellers through deals, automating manual sales actions while reducing the need for individual seller judgment in the sales process,” wrote Gartner.  Guided Selling is data and process-driven, with Next Best Action recommendations that make CRMs actionable.

Guided Selling intelligence is gathered from CRMs, emails, calendars, phone calls, and videos.  Engagement is measured across these channels and delivered as a set of insights and revenue signals that support Guided Selling.  Signals are Next Best Actions based upon AI recommendations and sales playbooks.  

Revenue Grid describes signals as “contextual, actionable notifications that tell your whole sales org what is going well or poorly throughout your whole sales process.”  Sales reps can act on recommendations by merely clicking on the signal.

These definitions can all get confusing, but the vision becomes clearer when skipping past the inputs and technology and merely considering which sales and management questions Revenue Grid looks to address.  Revenue Grid answers a host of sales rep questions, including

  • Which deals should I focus on today?
  • How likely am I to close the deal this month or quarter?
  • How can I improve my odds of winning this opportunity?
  • Which deals are at risk and why?  
  • Did I complete all of the post-deal activities discussed on the call?
  • Have I updated all my opportunities before tomorrow’s deal review?
  • How can I prepare for a meeting?
  • Does anybody at my firm have a relationship with key decision-makers?
  • How is engagement across the account?  Am I building relationships with the key stakeholders?

Likewise, managers can answer questions such as

  • Are sales reps focused on the right things?
  • Do sales reps know what to do next?
  • How can I guide reps in each deal?
  • Which deals are moving, stalled, or at risk?
  • Do my reps know what to say at meetings? Do our scripts work?
  • How do I know my coaching is effective?
  • Which committed deals are unlikely to close?
  • How do I improve our forecasts?

Part II discusses Revenue Grid’s feature set.

Clearbit for Clari

B2B Marketing Data vendor Clearbit partnered with Revenue Operations Platform Clari to deliver enriched contacts into CRMs.  Clari identifies external contacts from emails and meeting activity, helping fill out the buying committee.  According to Clari, only 30% of sales-engaged contacts are entered into the CRM.  By automating the contact identification process, sales reps have a clearer view of the full demand unit, allowing them to target messaging by function and recognize potential gaps in their knowledge of the buying committee.

By expanding knowledge of the demand unit, Clari can identify the broader set of decision-makers and reduce deal risk through multi-threaded relationship building.  Relying on one or two contacts has multiple risks:

  • The sales rep may not be messaging to the full demand unit
  • Their point of contact may be sidelined or leave the firm
  • Multiple points of contact may be set up dealing with different vendors, each providing a siloed perspective on the deal.
  • Post-sale, if users and administrators weren’t involved in the decision, adoption rates might be low, leading to higher churn rates.
  • The project champion may depart before renewal, forcing the rep to scramble to re-establish relationships at renewal time.

The expanded knowledge also helps marketing teams identify the key personas involved in deals and customize content and messaging.

“Now all the contacts that showed up for a sales meeting, even the ones that were added to the invite by the prospect, are automatically associated with the opportunity without your rep needing to lift a finger.”

Clari Marketing Programs Manager Maggie Kullman

Clearbit enriches the contacts with title, job function, and level. Firmographic and technographic details are also appended.

“As budgets get tighter and operating plans are reworked, having your prospects’ finance team involved early on is critical to accelerating the deal toward close,” wrote Clari Marketing Programs Manager Maggie Kullman.  “With the combination of Clari, Clearbit, and a little bit of automation, you can trigger an update to an opportunity field any time a CFO gets added to a meeting with the sales rep.  Now you can easily track which of your deals are missing a critical decision-maker and take actions to drive that relationship.”

Demand Units are a term coined by SiriusDecisions a few years ago when they updated their Demand Waterfall model for B2B sales and marketing. Each opportunity is associated with a set of decision-makers (e.g. technical, financial, functional directors) and influencers (e.g. users, admins). Demand Unit discovery is still in the early stages of development, but looking at email headers, out of office messages, and meeting attendees is a promising approach for organically identifying buying committee members.

Outreach KAIA Meeting Assistant

Sales Engagement vendor Outreach presented its 2020 product roadmap at its Unleash virtual conference.  The most compelling announcement was Kaia, its voice-enabled sales assistant that works alongside sales reps during video calls to record, transcribe, and deliver real-time assistance.  Other new capabilities include Sequence Intent Reporting, Outreach Voice Connectors, and Bombora Intent Scores.

“I’ve been waiting five years for Outreach Kaia.  This is the most powerful tool to be introduced in the sales industry in a long time, and we are very excited to be bringing the next generation of sales technology to life,” crowed Outreach CEO Manny Medina, who demoed the digital assistant during his keynote.  “Now more than ever, sales teams need Outreach Kaia — especially when so many of them are working remotely.  Outreach Kaia’s ability to surface real-time information exactly when a sales rep needs it during a live conversation is powerful.”

“Imagine you’re on a sales call, and someone asks you a question about your product or your competitor’s pricing, and you don’t know the answer.  Well, Outreach Kaia will automatically pull up the information you need – in real-time.  This level of intelligent assistance will make sales teams productive immediately.  Outreach already drives a nearly 5x return for our customers.  Now, with Outreach Kaia, we expect that ROI to soar.”

Outreach CEO Manny Medina

Kaia (Knowledge AI Assistant) delivers guided engagement for sales reps.  At the outset, reps are shown meeting and attendee information.  Tabs provide additional details on the account and opportunity, providing a quick pre-meeting review opportunity.  As the call gets underway, real-time transcription and analysis take place so that reps do not need to jot many notes during the call.  At any point, the rep can set a bookmark or add a short note.  As the note is stored in context, it might only require a word or two (e.g. Roadblock, Budget).  

Outreach Kaia operates as a real-time intelligent assistant that supports sales reps during customer calls. It transcribes the call, sets bookmarks for review, notes attendees and action items, and provides topical summary cards.

Kaia both records and analyzes the discussion, providing in-line prompts to the rep, such as a quick overview of a third-party mentioned during the call, short answers to technical and product questions, or objection handling tips.  The answers and objection handling are customer-defined, ensuring that company-specific details are displayed on a just-in-time basis.  Not only does each content card provide a technical and product backstop for new sales reps, but it allows experienced reps to speak with confidence on more technical details or dynamic topics from which they might shy away.

Content and people cards are trackable, “so managers can see which cards produce the best results and scale these insights across their teams,” wrote Product Storyteller Sunny Bjerk.

Kaia also notes action items during the call, again relieving reps of note-taking duties.  After the call, a summary is emailed to the rep with a set of action items, bookmarks, notes, and attendees.  The rep can then customize the document and share it with other stakeholders.

Kaia is displayed as a meeting participant, with attendees alerted at the beginning of the call that is it being recorded.  Transcripts and recordings are “securely stored within Outreach, which has enterprise-grade security measures already in place.”  Transcripts are available for training or review after the call.

Outreach Kaia is available for Early Access Signup for the summer 2020 beta and will be generally available in late 2020.  It is currently available for Zoom video conferencing with additional video partners in development.

SalesLoft Conversation Intelligence

Sales engagement vendor SalesLoft rebranded its Meeting Intelligence functionality as Conversation Intelligence.  SalesLoft describes four sets of features which help reps schedule meetings and then listen to, understand, and engage with customers and prospects.  SalesLoft supports a broad set of conversation tools including appointment setting; automated recording, transcription, and indexing of calls; time-stamped notes, and call analytics.  This functionality is available for prospect, customer, and internal calls.  Managers, mentors, and trainers can join calls or whisper into a sales rep’s ear.

“Through the evolution of SalesLoft’s platform and user experience, one feature has changed so much that its prior name no longer did it justice,” wrote SalesLoft Head of Community Aly Merritt.  “Meeting Intelligence is now Conversation Intelligence, because sales isn’t just meetings – it’s every conversation and interaction.”

Call recordings can be stored in a training library or shared for coaching or questions.  For example, if a sales rep does not know the answer to a question, it can be forwarded directly to customer support or engineering for a response.

Conversation Intelligence supports both SalesLoft’s native dialer and leading web meeting applications: Zoom, GoToMeeting, join.me, UberConference, Cisco WebEx, and Cisco WebEx Enterprise.

Sales calls come in many forms: prospecting, discovery, demos, stakeholder alignment, and so on.  All of these interactions make up the foundation for the long-term customer relationship.  High-value customer relationships are made possible when prospects feel that the relationship they are entering into is mutually beneficial.

How can you build such a relationship?  By working to ensure your prospects feel heard and confident that you understand their needs.  Work to engage them throughout their journey.  After all, sales doesn’t stop when the deal closes, nor does engagement cease when a seller hangs up the phone.

▪ SalesLoft Product News

SalesLoft said that it is “designed to flex around the needs of the user based not only on their role but also on their preferred workflow.  This empowers SalesLoft customers to offer consistent value at every stage.”

“Sales meetings are the moments in the sales cycle where you have the opportunity to provide the most value for your customers.  As such, they are some of the single biggest opportunities for your team to influence revenue.  It’s where your deals are won and lost,” wrote the firm.  “Despite this, sellers often don’t get the opportunity to improve on this critical component of the sales process.  Combine this with the challenges that face sales leaders around how much time it takes to digest sales meetings, gain visibility into what’s really happening, and be proactive in the deal cycle.”

Gong: Sales Rep Sins

Usually, I hate listicles. They are one of the laziest formats for blogging and feature articles, but Gong.io put the format to good use in a recent LinkedIn post titled “The 7 most horrifying sales call mistakes of 2019.” I would have gone with the “Seven Deadly Sins of Sales Calls,” but that is a minor editorial nit. Unlike most listicles, the post contained seven in-depth discussions of sales errors with supporting data.

And this data both supports the sales efforts of its clients and prospects and demonstrates the value of its Conversation Intelligence platform which assists with new rep onboarding and play recommendations.

Gong provides aggregated sales data to back up its statements.

For years, it has been gospel that sales reps should focus on a product’s unique value proposition and benefits. Features should be discussed when the prospect asks HOW, but should not be the focus of a sales pitch. In one graphic (see above), Gong has backed up this recommendation. What is amazing is how quickly a feature dump can sour a deal.

Feature dumping is to sales what bad breath is to dating. It kills “what could have been.”

Chris Orlob, Senior Director, Product Marketing at Gong.io

Chris Orlob, Senior Product Marketing Director at Gong, argues that “Most salespeople are overtrained on their products and undertrained on sales skills.”

My experience is different. It’s not that sales reps are overtrained on features, but that they aren’t trained in how those features map to benefits and their product’s value proposition. They also lack specifics around use cases and how their product provides value to specific industries. This causes them to take a least common denominator approach and hope a feature resonates. It’s the proverbial spaghetti on the wall. But this strategy leads to feature dumping and relying on your prospect to map features to benefits and benefits to value. Reps need more sales training, but they also need to understand their value proposition in the context of each prospect.

Sales reps that understand the concerns of their prospect by industry, job function, job level, and company size and can map those concerns to buyers across the buying committee don’t engage in feature dumping. They focus on their product value in the context of the customer. Features are discussed when they are must haves (“We are GDPR compliant”), but only in detail when the technical buyer or end user requests such details.

I don’t want to recapitulate what is a very strong post from Orlob. Instead, I recommend that you go see what he has to say about steamrolling objections, grand finale product demos, and four other sales sins.

People.AI Launches The Wire

People.AI announced availability of The Wire, their new artificial intelligence service for sales reps which suggests next best actions. According to the firm, “Like a brilliant personal assistant who’s always on top of his game, The Wire uses AI intelligence to remind you when to follow up on key accounts, suggest next-best-actions, warn you when a rep or account is falling behind, let you know when customer champions switch jobs, and ensure you’re always prepped for every meeting.”

The Wire suggests emerging opportunities, opportunities requiring attention, and champions that have departed to other companies.

The Wire flags opportunities that are in jeopardy of slipping due to inaction.
The Wire flags opportunities that are in jeopardy of slipping due to inaction.

Managers are alerted when sales reps are falling behind targets.  A Rep Ramp Alert “helps you move from data-aware to data-driven, proactively leveraging industry data to guide and coach your teams.”

Ramp Alerts identify reps that are lagging behind best-in-class recent hires and suggest when a one-on-one meeting may be required.
Ramp Alerts identify reps that are lagging behind best-in-class recent hires and suggest when a one-on-one meeting may be required.

The Wire also supports meeting intelligence with meeting prep reminders and post-meeting note capture and CRM sync.


Last Friday, I covered People.AI’s Round C and the company more broadly.

Drift Unlimited Contacts

Conversational Marketing vendor Drift is moving away from volume-based pricing and offering unlimited contacts for its chat platform.  Volume pricing places pressure on marketing departments to trim the number of contacts in their databases to stay below volume thresholds.  By moving to unlimited leads, marketers can better forecast their budgets and avoid panic as they approach volume limits.

“Why should companies punish you for growing?” blogged Senior Director of Demand Generation Kate Adams.  “After all, that’s the promise most software products these days make.  Use our service and you’ll grow your business faster.  Install our product and your conversion rates will skyrocket.”

“Because you’ve spent YEARS building up your database.  And now you need to decide if contacts that are 1 year old or 6 months old or 3 months old make the cut.  You’re literally washing money down the drain.  What if the leads you’re throwing in the trash to keep your marketing budget below your benchmark are actually just higher up in your funnel?  And require more nurturing and education about how you can help them solve their problems?”

Drift Senior Director of Demand Generation Kate Adams

Drift also announced a Drift Meetings feature which allows prospects to schedule meetings directly from the company website via a “book a meeting” call to action.  Meetings can also be booked by chatbots, and sales development reps can qualify a lead during a live chat and book meetings on behalf of account executives.

“With Drift Meetings, you can target your best visitors and ABM accounts, welcome them with a personalized message from the right rep, and let them instantly schedule a meeting right from your website,” says the firm.

Calendar seats are priced at $20 / seat / month.

Drift has 220 employees and 150,000 customers.