Technical Support at an AI Company

 

Technical Support at Conversica (The Wins)

I had committed to 5 years, and even though I didn’t envision it taking as long as it did, we finally achieved most of what we originally set out to accomplish back in October 2019.

When I took the helm in 2019, Conversica’s Technical Support (TS) function was built for speed, not scale. Rooted in reactive support for a high-volume SMB base, the team was measured by ticket deflection, not customer impact. Fast forward to 2025, and TS had become a linchpin for our enterprise readiness and retention engine.

The transformation began with a mindset shift—from fixing issues to enabling outcomes. We restructured TS around issue resolution quality, first-response time, and most importantly, customer value preservation. Instead of being the team that dealt with noise, TS became the team that sustained ROI.

A major catalyst: the internal adoption of Conversica itself. Using our AI agents, we automated triage, pushed proactive alerts based on telemetry, and even had agents request feedback after key support interactions. This freed up human engineers to focus on root cause analysis and high-complexity escalations, rather than ticket traffic control.

We also introduced a tiered support model, aligned with customer segmentation. Strategic accounts received designated Technical Account Managers (TAMs) who bridged CS, Product, and Engineering. For smaller customers, we scaled service through contextualized knowledge bases, diagnostic bots, and automated follow-ups—cutting resolution time by 30%.

Lastly, TS wasn’t just supporting—it was signaling. Weekly synthesis of top issues fed directly into Product’s roadmap prioritization. That tight loop—Support → Insights → Action—meant fewer recurring bugs, better documentation, and smoother releases.

Technical Support – Strategic Headwinds (The Losses)

Despite our gains, we hit walls—particularly in scaling for enterprise expectations.

  1. Support ≠ Success
    In many cases, customers blurred the lines between Technical Support and Customer Success. We hadn’t clearly defined boundaries. As a result, TS was asked to “go beyond the ticket,” handling onboarding gaps, configuration advice, and even AI performance questions. This diluted focus and stressed resourcing.
  2. Global Support Wasn’t Global Enough
    Our expansion into EMEA and LATAM was ahead of our support infrastructure. Time zones, language coverage, and localized content were reactive rather than proactive—leaving some international customers underserved and creating perception gaps in reliability.
  3. Talent Depth Lagged Behind Tech Complexity
    Our own evolution—from template bots to next-gen conversational AI—outpaced the capabilities of our frontline support team. Troubleshooting model accuracy isn’t the same as debugging a customer’s custom workflows and associated conversation rules. We didn’t upskill fast enough, and it showed in escalations and time-to-resolution for complex cases.

Advice From One CEO to Another – Building Technical Support for AI Scaleups

  • Draw the Line Early
    Don’t let support become a catch-all. Create clear charters for TS vs. CS vs. PS. Clarity protects quality—and employee sanity.
  • Invest in Tooling as Much as Talent
    A good support engineer is gold—but one with automated diagnostics and CRM-integrated insights is platinum. Your stack matters.
  • Treat Support Tickets as Product Data
    Support is the smoke before the fire. Design systems to capture trends early and route them into weekly product and engineering reviews.
  • Use Your Own Product Religiously
    We used Conversica agents inside support, with a chat-based AI agent trained on all our product knowledgebase. It gave us leverage, credibility, and direct feedback on our own product—priceless.
  • Certify, Don’t Just Train
    AI support isn’t generalist work. Build certification paths tied to product tiers, use cases, and verticals. Make expertise measurable.
  • Make TS Part of Your Strategic Narrative
    Don’t bury support behind success. Showcase the function as a retention driver and trust builder—especially in board decks and investor narratives.

Conclusion

By 2025, Conversica’s Technical Support function was no longer the last line of defense—it was the silent engine sustaining long-term customer value. We moved from being measured by ticket volume to being celebrated for renewal impact. We weren’t perfect, but we were strategic.

The customer’s Technical Support team isn’t where customers go when things go wrong. It’s where they discover you’ll never leave them behind.

 

Jim Kaskade

Jim Kaskade is a serial entrepreneur & enterprise software executive of over 38 years. He was the CEO of Conversica, PE-backed leader in AI Automation solutions that help clients grow revenue. He successfully exited PE-backed SaaS company, Janrain, in the digital identity security space. Prior to identity, he led a digital application business of over 7,000 people ($1B). Prior to that he led a big data & analytics business of over 1,000 ($250M). He was the CEO of a Big Data Cloud company ($50M); was an EIR at PARC (the Bell Labs of Silicon Valley) which resulted in a spinout of AML AI company, Quantiply; led two separate private cloud software startups; founded of one of the most advanced digital video SaaS companies delivering online and wireless solutions to over 10,000 enterprises; and was involved with three semiconductor startups (two of which he founded, one of which he sold). He started his career engineering massively parallel processing datacenter applications. Jim holds an Electrical and Computer Science Engineering degree from University of California, Santa Barbara, with an emphasis in semiconductor design and computer science; and an MBA from the University of San Diego with an emphasis in entrepreneurship and finance.

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