International Operations at an AI Company

 

International Operations 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 joined Conversica in late 2019, our international footprint was barely more than a dotted line on a strategy slide. We had General Managers in LATAM and EMEA, but no integrated strategy, no repeatable GTM model, and little to no revenue outside North America. It was more ambition than execution.

By 2025, while Conversica didn’t become a global juggernaut, we had successfully transitioned from a scattered “global outpost” model to a scalable, partner-led, tech-enabled framework. International ARR was still small, but the conversion efficiency, customer health, and partner leverage had all dramatically improved.

What changed? First, we shut down the fantasy of field-led international expansion. Regional GMs were sunset, and we shifted to embedded alliances, digital delivery, and AI-first scale. Instead of boots on the ground, we leaned on product and partnerships to open doors—localization via platform, not personnel.

Second, we applied a “Conversica on Conversica” approach: our AI agents were deployed internationally before our sales team ever stepped foot there. This allowed us to validate use cases, learn cultural nuances, and optimize messaging at scale—before committing dollars.

Third, we pivoted to indirect channels. We used strategic SIs, VARs, and embedded tech partnerships to create footprint without overhead. This shift turned international from a capex drag into a margin-positive growth path.

Most importantly, we realized that global readiness isn’t optional when pursuing large enterprise accounts. Even when headquartered in North America, our top customers required regional support across LATAM, EMEA, and APAC. That’s why our PLG (Product-Led Growth) + Partner-Led model became so pivotal—giving us international reach without the burden of international infrastructure.


International – Strategic Headwinds (The Losses)

We took our hits along the way:

“ROW = Rest of Worries”

International revenue never exceeded 2–5% of total ARR even by 2024. Despite the strategy pivot, international remained a rounding error—a sobering reality that forced us to rethink resource allocation.

The GM Model Failed Us

Our early approach relied on regional GMs with unclear charters, limited resources, and misaligned incentives. LATAM and EMEA floundered with low traction.

Product-Market Fit Was Assumed, Not Proven

We initially assumed our success in North America would translate easily to other markets. It didn’t. Messaging, integrations, and even use-case relevance varied dramatically across geos.

Compliance & Complexity Slowed GTM

GDPR, data residency, and local tax regulations turned simple deployments into complex hurdles. We underestimated how much operational drag international expansion would introduce.


Advice From One CEO to Another – Global Without the Bloat

Start With Product, Not People

Test demand through self-service, digital campaigns, and AI-led POCs before building teams. Let usage signal readiness.

Kill the “Global GM” Fantasy

Unless you’re doing $200M+ ARR, don’t build international fiefdoms. Hire partnerships, not presidents. Global growth should be plug-in, not top-down.

Use Partners Like Multipliers

Your best international sellers won’t be employees—they’ll be ecosystem players. SIs, VARs, and tech alliances are your early salesforce.

Make International a Feature, Not a Function

Global readiness should be built into your platform—multi-language, GDPR-compliant, timezone-aware. Don’t bolt it on later.

Keep KPIs Local but Insight Global

Track usage, churn, ACV, and CAC by region. But roll them into one source of truth so strategy stays unified.


Conclusion

We didn’t become Salesforce International—but we did something more important: we made international repeatable, scalable, and sane. By 2025, we had a model we could extend without betting the farm. That’s more than most startups can say.

The lesson? International isn’t about going everywhere—it’s about growing the right way, in the right places, at the right time.

And when your customers span the globe, your strategy must too—not with bodies, but with systems, partners, and platform leverage.

Global ambition without local execution is just a passport stamp. So speak the language, scale with leverage, and never confuse global presence with global impact.

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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