Interview

AITech Interview with Jim Kaskade, CEO at Conversica

AI is redefining sales and marketing by enhancing engagement, automating outreach, and driving revenue growth with unmatched efficiency.

Jim, could you start by telling us about your journey to becoming the CEO of Conversica and what drives your passion for the role?

I was asked, by our Private-Equity investors, to take a look at Conversica & provide my perspective, 5 years ago. Who would have known that my strong opinions about the business would result in them offering me the opportunity to turn perspective into action.  

I was looking through three lenses, each fueling my passion for the Company: 

  1. Having run Digital Applications at DXC, a large system integrator, we deployed over 1,000 digital transformation projects each year. During this time, it was obvious that all improvements in digital touch resulted in significant internal hurdles for revenue teams, all struggling with the increased digital volume. I was excited by the idea of a world where back office RPA and front office AI agent automation would come together to create an end-to-end intelligent automation solution. Now, we see that AI Agent Frameworks are reaching across ALL business functions, with our focus in the front office for marketing, sales, and customer success, Conversica enjoys boosting revenue (rather than solely reducing costs).
  2. Also, having run a Big Data & Analytics team delivering several hundred advanced analytics projects per year, we were using the latest in machine learning / deep learning technologies. I knew of the transformer breakthroughs (GPT-1, and BERT back in 2019 before I joined). What excited me was the potential to truly disrupt customer experiences with GenAI. We started development the week I joined and then launched our first GenAI solution in March, 2020.
  3. Lastly, I saw an opportunity to solve a really hard problem – namely, addressing the needs of large enterprises (Fortune 500) with AI automation (not the small businesses), carefully deploying the latest in AI technology, but in a way that would guarantee 100% brand safety (a clear requirement for large enterprises). Today we are providing solutions for the largest and most highly regulated companies with AI solutions that are 100% safe to deploy, and at scale.

How have you observed AI transforming the way sales and marketing teams operate, particularly in overcoming seasonal sales slumps?

Marketing is under pressure to deliver high-quality leads to sales with small teams and small budgets. Sales is under pressure to grow revenue, fielding a delicate balance between inbound and outbound pipeline generation. By deploying AI automation, marketing can scale at a fraction of the cost, delivering only “sales-ready” opportunities, which sales teams can now focus on, creating high-quality relationships versus simply blasting target lists. For the first time both teams can come together with a single purpose – weave in AI with existing teams to create a new type of growth workforce. Specifically, we’re seeing 30% lead follow-up turning into 100%; 38% open rates turning into 80%+; click-throughs going from 1%+ to 19%+; a two-way engagement with 24% of those the AI reaches out to; and most importantly 10%+ success in reaching the goal an AI was intended to accomplish. Conversion rates are unbelievable. Oh, by the way, I’m quoting the average across the network, not the best case. 

In your opinion, what are the biggest challenges that CMOs and CSOs face during these slow sales periods, and how can AI alleviate some of this stress?

Revenue growth is hard. The biggest challenge for C-suite is understanding where and how to deploy AI automation. For revenue teams,  you can provide insights to your sellers, AND you can augment your sellers with AI-enabled selling velocity. This means that AI can be either your “co-pilot”, giving suggestions to the sellers; or this means that the AI becomes a seller (aka “pilot”) engaging your customer prospects and existing customers directly. The idea of putting your most important asset, customers, in the hands of AI is scary. So, how does c-suite get comfortable with this, especially if the AI goes rogue? Answer, you can’t unless your vendor/partner can guarantee “brand safe” AI experiences. This is where Conversica excites me the most. We’re the Forrester Wave leader because we’re 100% brand safe. Period.

Could you share how AI is helping sales teams proactively engage with potential buyers and how this impacts overall sales performance?

Rachel is your BEST employee. She engages your prospect clients who are simply discovering your brand, learning about you. She can also field any question about your products and services with information about your business at all depths. She can outbound, turning outreach into high quality inbounds. She knows how to warm up target accounts for your sales team. She can also go after aged lead stock, driving new interest. Any former customer that you lost, is a target she loves to reenergize. She also knows how to have authentic conversations with any type of customer at any level, building rapport, and surfacing handraisers. She knows how to pre-qualify, validating fit, and then scheduling only the right candidates for sales meetings. Post-transaction, she will proactively engage & schedule account reviews, reach out if she sees your adoption dropping, identify and personalize upsell and cross sell opportunities, facilitate timely renewals and expansion discussions, and even check in and collect feedback from customers in beta or trial experiences or generally in their product/service journeys. All this sounds amazing. But even more amazing is that she’s an AI. AND, she is driving an average of 24X on ROI in real revenue (closed business), not just pipeline. Again, that is our average across our network!

How do you see AI’s role in improving the efficiency of prospecting and cold calling for sales teams?

We recommend placing EVERY inbound lead into the hands of your AI. He/she can make sure that your sales teams ONLY field customer prospects who are 100% in-market. Then, after focusing your sales team by removing all the “tire-kickers” from their “first meeting” lists, you can attack prospecting. The best practice here is to have your sales team do the homework on their targets, researching who in the organization is the right fit for your product, and collecting critical information on them. Even have your sales team make the first outreach for these targets. But then, hand those leads you initially touched to your AI – your personal assistant who is following up and driving a two-way conversation through the discovery and qualification process. Then your sales team is freed up to finding more gold, building and adding to the target lists. Think about it, you do your highly targeted research, studying earnings calls, observing social media mentions, trying to learn about the priorities of your targets – collecting the personalized view. Then allow your AI to take that information and run with it, only to hand that lead back to you once they are SALES-READY. Sales productivity goes through the roof, and supporting that, reduced sales cycles, and increased win rates.

In what ways does AI contribute to optimizing the scheduling of appointments, allowing sales professionals to focus more on revenue-generating activities?

Scheduling appointments” is the low bar. The high bar is handling a sequence of dynamic steps towards a goal which, by definition, is complex. Imagine you are a $60B B2B software giant (one of many of our clients), or you are the largest multinational payment card services corporation in the world (again, one of our clients). You want to sell complex products and services to buyers who have complex requirements. Now, how do you guarantee that your AI represents your global brand appropriately? How do you step people through their buyer’s journey seamlessly, WITHOUT error? And how do you make sure your sales teams don’t feel like your AI is MESSING it up?!!! AI can take qualification frameworks, like BANT and ANUM, or sales methodologies like Challenger, Sandler, Spin, or MEDDPICC, and literally perfect them, with consistent process, and consistent messaging. And it can do so, while guaranteeing brand-safe interactions (yes, your AI councils, legal, and security teams are going to be happy).

How does AI assist in handling routine tasks like answering FAQs, and what benefits does this bring to marketing teams?

Imagine taking every bit of your corporate website content, in every language, with every product and service; along with all your knowledge base articles; all your corporate sales and marketing documents; customer training videos; podcasts…ALL your external-facing media and giving that to your AI – private AI. Now, FAQs are at the digital fingertips of your AI for any dynamic exchange anywhere in the world at any point of the sales process. It is not only what Marketing teams who can benefit from this, but sales and customer success teams too. 

What strategies would you recommend to sales and marketing leaders looking to fully leverage AI to boost their team’s productivity during slower sales cycles?

Don’t view this as a “slow sales cycle” booster. View this as a way to stay ahead of your competition during bear and bull markets. If you’re growing, grow faster. If you aren’t growing, ignite the growth. If you are growing fast, but not in a capital efficient manner, then leverage this for profitable growth. Strategies involve: a) start with ALL inbound traffic; b) then add all your outbound, then c) apply to the base of existing customers. It’s a 1, 2, 3 strategy, and it works. Also, don’t be afraid of GenAI. There’s a very clear way of repeating the era of “public cloud” vs. “private cloud” in the AI world – namely, instead of putting all your data in the “public GenAI” provider’s hands, let us create a “private GenAI” solution for JUST you. We can guarantee 100% brand safe, 100% AI Act compliant, GDPR compliant, etc.

As the adoption of AI in sales and marketing continues to grow, what new trends or innovations do you foresee emerging in this space?

GenAI is here to stay. BUT, there’s one end of the spectrum for the highly-governed, where you need 100% deterministic and controlled versus at the other end of the spectrum where the AI has full flexibility and ability to dynamically engage. In either case, we can provide you 100% brand safe…so you are able to “dip your toes” and then add more as you gain confidence. If we had focused on simply developing a nice user interface on top of OpenAI (think every new entrant in the GenAI space, or even the more mature with recently announced CRM Agent Frameworks), they are all missing the true F500 requirements. Sure, “ground” your LLMs, and “redact” PII and PHI. But where the true challenge exists above these “table stakes” is making sure your AI never confabulates / hallucinates. That is where the true magic is delivered. As of this writing, we’re the only one who can deliver the best end-customer experience with client-safe GenAI solutions which will not get management or the board in trouble. Just ask yourself, who in the revenue AI solution space had launched a large language model capability back in 2019, just two years after the transformer was invented? I know of only one.

Now, where does this go? We are 6 orders of magnitude beyond where AI was when we first introduced our first Sales AI in 2009. We only have 2 orders of magnitude to go before our AI is as intelligent as the human brain (100T synapses and 2.5GB of memory). So in 1-2 years, maybe 3, AI reaches and begins to surpass our reasoning and knowledge base levels, as humans.

You can begin to dream about what’s possible, and I say it’s a reality. Dreams turn into reality in 3 years, minimum, across the most sophisticated multi-step business processes.

Finally, what are your aspirations for Conversica in the coming years, especially in terms of helping companies overcome the challenges of sales slumps?

I watch Salesforce with Agentforce, and Microsoft with Magentic-One, not to mention the plethora of others who are piling in on the Agentic Framework bandwagon. Conversica only benefits from the innovations of these frameworks, and their underlying LLM providers (OpenAI, Meta, Google, Mistral, Anthropic, xAI). The truth, we are focused on “AI Applications” not AI plumbing/infrastructure. Our objective is to solve business problems, providing customers with “out-of-the-box” solutions that are code-free. Thus, companies who want profitable growth, without huge time and dollar investments to get their first AI Agent into production, will come to us. After the world appreciates that time is money in this world of AI technologies too, they will stop playing around with APEX, LWC, Visualforce, SOQL, SOSL, etc…. and show their boards value quickly. The hype cycle is over, and the trough of disillusionment has begun. Let the agent wars play out.

Jim Kaskade

CEO at Conversica

Jim Kaskade is the CEO of Conversica, a leader in AI-powered Revenue Digital Assistants for revenue-generation use-cases. With over three decades in technology leadership, he has spearheaded innovations in artificial intelligence, big data, and digital transformation.

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