SalesTechStar Interview with Jim Kaskade, CEO at Conversica

The future of marketing and sales will be driven by conversational AI; Jim Kaskade, CEO at Conversica highlights why while talking about the power of conversational experiences in digital marketing and sales today:


Welcome to this SalesTechStar chat Jim, tell us more about yourself and how your journey as CEO at Conversica has been?

I’m literally pinching myself…this is a DREAM job, truly. OMG I LOVE this company…and there’s one simple reason for that – OUR PEOPLE ROCK!

We’d love to hear about some of Conversica’s recent enhancements and company changes?

Digital-first is now the norm, and customers expect businesses to deliver a personalized, cohesive online experience. As a matter of fact, most realize that they have to compete based on customer experience. 

Our product enhancements in 2021 were focused on enabling businesses to deliver a consistent, prompt, personal engagement throughout the buyers’ journey with AI automation. Our AI-based digital employees work tirelessly for almost 2000 global enterprises, specifically for marketing, sales, and customer success teams.

Before I started in late 2019, I presented a 5-year strategy and plan for the business. 2020 was the year of “Revenue Diversity,” and 2021 was the year of “Ecosystem Partners.” 2022 is the year of “Community”; 2023 will be about going global more aggressively; 2024 will be about maturing our business in preparation for an IPO. 

So with confidence, I can say the only consistent thing here is change, positive change. We have recently welcomed new members to our team, including Mark Cuny as Chief Financial Officer, Ella Dillon as Chief Customer Officer, Terrie Banuelos as Vice President of Global Sales, Lewis Barr as Vice President of Legal and General Counsel, Joshua Fox as Vice President of Alliances, and David Greenberg as Chief Marketing Officer. These leadership additions position Conversica well to help disrupt enterprise marketing, sales, and customer success teams in our digital-first world. The next big move for the company is the size of businesses we’re focused on enabling now. We’re determined to capture at least 50 of the fortune 500 before we IPO.

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What’s in store through 2022 (in terms of exciting updates/and more) for users of the platform?

For our clients, we have been making investments in “re-imagining conversations” between our AI and end-users. We believe that the AI industry needs to direct its focus on making AI smarter, more human-like, and more natural. We’re also focused on “PLG” or Product-Led Growth. This translates into making our AI simpler to deploy by our customers and partners (for their customers). It only takes hours to deploy our AI today, using our library of over 600 out-of-box conversations. So with such simple deployment, our definition of PLG means allowing others to innovate on their AI conversations more easily. Lastly, product enhancements include expanding our portfolio of offerings. Here are a few examples of this…

Account-Based Marketing (ABM) has emerged as an essential go-to-market strategy in today’s digital age, which is why we recently announced new Conversational ABM capabilities through Conversica’s AI Assistants. The solution combines the value of personalized human dialog with the prompt, persistent, and consistent engagement of Conversational AI with the power of ABM from leaders such as 6Sense, Demandbase, and Terminus. This means enabling sales and marketing teams to execute ABM at scale, incorporating intent data into AI conversations, leading to unmatched engagement, accelerated deal cycles, and better customer experience for every account.

We also reinforced our strategy to provide Conversational AI solutions across the entire customer revenue lifecycle by offering Conversational Customer Success. This is the first in the industry. Our AI Assistants for Conversational Customer Success help highly leveraged customer success teams drive customer health and business outcomes, allowing companies to realize a significant increase in CSM capacity while improving customer relationships. In the end, gross retention and net retention rise significantly.

Another significant investment involves moving into Conversational Commerce. Given our decade focusing on sales, we felt it was important for us to invest in digital commerce as a growing sales segment. Digital-first B2B and B2C enterprises embracing e-commerce know the value of improving customer experience with a digital concierge. Most companies use live chat solutions that connect prospect buyers to contact centers. However, we believe that a digital concierge is a complementary solution that will scale.

How in your view will conversational AI grow in impact through 2022? What predictions do you have for these technologies?

The acceleration of a digital-first world will continue into 2022, and Conversational AI will be the only way to provide scalable personalized experiences for end-consumers throughout their digital lifecycle. Despite the challenges, the new year holds new opportunities for businesses digitally innovating to meet the future. Here are a few of my predictions for the year ahead:

Digital Investments Will Expand Beyond Sales to the Entire Buyer Journey 

“Buyer’s Journey” is now the new “Digital Transformation.” When looking at the buyer’s journey, AI has significantly impacted the sales function, helping drive more deals and revenue. However, we believe that in 2022, more organizations will be focusing their customer experience (CX) investments across ALL touchpoints along the revenue lifecycle, starting in marketing, expanding in sales, and next in customer success. This creates a consistent experience end-to-end, from discovery through advocacy. Companies will recognize that they can get more qualified leads by nurturing relationships early on in marketing with personalized conversations. But imagine the value you can create by applying AI to customer success – companies can meet the needs of their existing customer base, mitigating churn, expanding relationships and generating more long-term growth.

AI Will Help Address Talent Shortages and Augment Existing Team and Workflows

In 2022, companies will continue to strive for exceptional customer experiences. But with GDP growth slowing, budgets will continue to be constrained. How do enterprises service the modern consumer who now expects a hyper-personalized concierge service at every interaction throughout the buyer journey? These interactions are increasingly happening digitally (via chat, SMS, social messaging and, of course, email), making a strategy for digital transformation and customer journey optimization one of the highest priorities on corporate agendas. Companies are now asking, “Where can we further automate and apply AI for customer experience? How do we best engage with customers in all digital workflows? How can we stay competitive at scale?”

We believe that to scale digitally and ensure that each customer enjoys a positive digital experience, we’ll see a gravitation towards digital-to-AI workflows, augmenting the existing digital-to-live agent workflows. And ultimately, by leveraging the power of Conversational AI, revenue-generating teams will also be able to do more of what they do best versus supporting repetitive and mundane tasks.

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Can you talk about some of the ways in which you’ve seen leaders across different segments implement conversational AI assistants for different purposes?

The most impressive deployment that we are seeing is global, with over 1,000 AI assistants covering 13 different countries (and languages), 27 different product BUs, nine different industries, and 16 pre-sales and post-sales use-cases. So leaders are simply adopting. Here is an overview of some powerful use-cases:

  1. Engage Suspects Based on “Intent” data
  2. Engage Targeted Accounts with Sales Plays
  3. New Lead Eligible Responses 
  4. Pre-Event Outreach to Drive Attendance 
  5. Post Event Follow-Up (e.g., No shows)
  6. Re-engagement of retired leads
  7. Engage Opportunities Stuck at 10-30%
  8. Trial Activation and Conversion
  9. Lost Customer/Winback
  10. Lost Customer/Feedback Requested
  11. Subscription Renewal
  12. Drive Advocacy/Net Promoter Score (NPS) Feedback
  13. Health Check Review
  14. Expand Usage/Product Announcements
  15. At-Risk Subscribers: No / Low Usage Cloud Credits
  16. Onboarding/Education

A few thoughts on how you feel salestech as a segment will move in 2022?

We see an opportunity for consolidation within the salestech segment. For example, sales enablement platforms (SEP providers like are well-positioned to add or merge with conversational analytics solutions (voice call analysis leaders like ABM can be applied not only to pre-MQL activities but to sales development as well. 

That said, marketing automation, SEP, CRM, and customer success platforms all need to integrate with ABM platforms and leverage intent data to better inform with deeper insights. 

Lastly, like ABM, AI can help inform revenue teams with improved analytics around the funnel. However, AI can also be applied actually to take action based on those new insights.

Some last thoughts, takeaways and B2B best practices before we wrap up!

B2B marketing, sales, and customer success leaders will significantly impact their businesses as they apply AI to meet the digital native’s demands. AI will be used not only to create more insights across the B2B funnel but also to take action on those insights.

Do you think that you can deliver digital experiences with non-digital solutions? I believe that combined human and AI automation solutions are needed to truly disrupt the revenue lifecycle.

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Conversica is a leading provider of Conversational AI for business, helping organizations augment their workforce to attract, grow and retain customers.

Jim Kaskade is the CEO at Conversica

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