Crawl, walk, run: starting digital transformation

This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.

Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the old reactive, relationship-based CS model is no longer cutting it.

At Sophos, the threat landscape is compounding fast. AI is accelerating the speed and sophistication of attacks, which means response times, customer journeys, and success motions all have to evolve in lockstep in order to keep up. Teresa has spent her career at companies like Zendesk, Autodesk, and ON24 building the operational frameworks that make that possible at scale.Mentioned Resources: Cleverbridge: Merchant of Record for Software & SaaS​Guest links:

Teresa Anania - LinkedIn: https://www.linkedin.com/in/teresa-anania/

Sophos - LinkedIn: https://www.linkedin.com/company/sophos/

Sophos - Website: https://www.sophos.com/

Host links:

Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona

Newsletter: https://thegtmnewsletter.substack.com

Sponsors:

- HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/

- Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, research, and sequencing so reps can focus on conversations. Learn more at https://www.nooks.ai/

- Cleverbridge – the digital commerce platform helping enterprises optimize post-sale revenue through renewals, winbacks, and add-ons with buyer-friendly purchasing experiences. Learn more at https://grow.cleverbridge.com/lp/digital-commerce

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

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Highlights:

00:00 – Sophos at a glance: 600K customers, $1B+ in revenue, and why cybersecurity keeps growing when everything else slows down01:51 – AI vs. AI: how threat actors are using the same tools Sophos is building against03:02 – The 2026 Active Adversary Report: why attackers are logging in, not breaking in04:20 – Attackers move in 3-4 hours and how Sophos structures CS to respond before the customer even knows there's a problem06:05 – Connecting CS activity directly to retention and expansion: the attribution model08:45 – Advice for early-stage companies that want this kind of rigor but don't have perfect data yet10:06 – Automation as a scale lever: crawl, walk, run and why you should start at the end of the renewal cycle13:43 – The future of go-to-market: self-serve from first touch through win-back, powered by AI18:20 – "The customer should never feel your org chart": building a digital journey that meets people where they are20:39 – Going from legacy manual to digital without blowing up the business22:00 – Dynamic segmentation: why hard lines on ACV are the wrong way to assign CS coverage26:02 – The two-by-two that actually matters: risk, spend, and growth potential32:08 – The humble confidence hire: why Teresa looks for this specific combination across her entire org34:15 – The 5-to-1 scorecard and what Teresa has learned about earning customer trust over time36:14 – Inner and outer feedback loops: how Sophos turns NPS data into cross-functional action38:11 – Why retention has to be an all-company meeting, not a CS slide

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