Also this week: we welcomed Jason Demant as Partner, Head of Networks at GTMfund. We shared more context in a bonus episode, watch here.
Brought to you by:
If you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next.
HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale what works. That’s why teams like RingCentral, Outreach, ActiveCampaign, and Fortune 100 companies rely on HockeyStack to eliminate wasted spend, take better decisions, and make space to think.
Learn more at hockeystack.com
Outbound sales today is still built around manual work: writing emails, building lists, and managing sequences across disconnected tools.
Nooks is breaking the mold. With their new AI Sequencing product, Nooks is an agent workspace where AI works alongside reps, helping them understand accounts, prioritize the right prospects, and generate context-rich outreach based on actual first-party interactions.
No more wasting time in multiple tools - it’s one unified workspace for all your outbound channels. Arm your sales team with intelligent outbound. Learn more at nooks.ai.
A clear shift is underway in enterprise software. More companies are rethinking how they segment customers and structure servicing models — especially in post-sale motions like renewals, winbacks, and add-ons.
For too long, too much lower-touch revenue has been routed through direct sales or partner motions where the cost-to-serve doesn’t match the value delivered. Increasingly, companies including Sophos, SUSE, and PTC are using Cleverbridge to move more routine transactions into digital, buyer-friendly purchasing paths while reserving high-touch resources where they add the most value.
If you’re rethinking customer segmentation, servicing models, or how digital and AI should apply across your customer base, Cleverbridge is worth a look. Learn more at grow.cleverbridge.com/lp/digital-commerce.
Who we sat down with
This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint, another Thoma Bravo portfolio company. 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.
Discussed in this episode
Why AI-accelerated threats have made “always on” customer operations a baseline requirement
How Sophos structures customer success to respond before a customer even knows there’s an issue
The attribution model Teresa uses to tie CS touchpoints directly to retention and expansion
Why waiting for a support ticket is too late
The crawl, walk, run approach for early-stage companies that want to build CS rigor without perfect data
How dynamic segmentation (not just company size) determines coverage models and CSM assignment
What “humble confidence” looks like as a hiring bar and why Teresa uses it across her org
Why retention has to be an all-company play
The role of inner and outer feedback loops in turning NPS data into cross-functional action
How to start the digital journey transformation without disrupting the core business
Episode highlights
00:00 – Sophos at a glance: 600K customers, $1B+ in revenue, and why cybersecurity keeps growing when everything else slows down
01:51 – AI vs. AI: how threat actors are using the same tools Sophos is building against
03:02 – The 2026 Active Adversary Report: why attackers are logging in, not breaking in
04:20 – Attackers move in 3-4 hours and how Sophos structures CS to respond before the customer even knows there’s a problem
06:05 – Connecting CS activity directly to retention and expansion: the attribution model
08:45 – Advice for early-stage companies that want this kind of rigor but don’t have perfect data yet
10:06 – Automation as a scale lever: crawl, walk, run and why you should start at the end of the renewal cycle
13:43 – The future of go-to-market: self-serve from first touch through win-back, powered by AI
18:20 – “The customer should never feel your org chart”: building a digital journey that meets people where they are
20:39 – Going from legacy manual to digital without blowing up the business
22:00 – Dynamic segmentation: why hard lines on ACV are the wrong way to assign CS coverage
26:02 – The two-by-two that actually matters: risk, spend, and growth potential
32:08 – The humble confidence hire: why Teresa looks for this specific combination across her entire org
34:15 – The 5-to-1 scorecard and what Teresa has learned about earning customer trust over time
36:14 – Inner and outer feedback loops: how Sophos turns NPS data into cross-functional action
38:11 – Why retention has to be an all-company meeting, not a CS slide
Key takeaways
1. If you’re waiting for a ticket, you’ve already failed your customer.
By the time a customer inbounds a problem, you’ve already missed a window. The best CS orgs are predictive. They identify where customers get stuck, build curated digital journeys around those moments, and intervene before the customer even knows they need help. That’s what “always on” actually means.
2. CS only drives revenue when it’s outcome-based, not relationship-based.
The old model (check-ins, QBRs, account health scores) isn’t cutting it anymore. Teresa builds attribution models that correlate specific engagement touchpoints to retention and expansion. You can’t improve what you can’t measure, and most teams aren’t measuring the right things.
3. Dynamic segmentation beats static ACV tiers every time.
Hard lines on company size or contract value lead to misallocated coverage and missed growth. The better model? A two-by-two of current spend, risk, and expansion potential that flexes every few months as customer health changes. Your best CSMs should be matched to the accounts with the most upside, not just the biggest logos.
4. Don’t just treat retention as a CS swim lane.
Teresa runs a monthly cross-functional meeting with product, marketing, sales, and support to action NPS insights together. The inner loop closes individual feedback fast. The outer loop informs strategy. Most companies say retention is everyone’s job. Few actually set it up that way.
5. Start at the end of the renewal cycle, not the beginning.
When building a digital CS motion from scratch, Teresa starts with win-back and renewal, not onboarding. That’s where you can show near-term impact, identify churn culprits, and build the playbooks that eventually get you to a proactive, full-lifecycle motion. Crawl, walk, run.
Follow Teresa Anania
Sophos’ LinkedIn: https://www.linkedin.com/company/sophos
Sophos’ Website: https://www.sophos.com
Verint’s LinkedIn: https://www.linkedin.com/company/verint
Verint’s Website: https://www.verint.com
Follow Sophie Buonassisi (Host)
X (Twitter): https://x.com/sophiebuona
Newsletter:
Follow GTMnow
LinkedIn: https://www.linkedin.com/company/gtmnow
X / Twitter: https://x.com/GTMnow_
YouTube: https://www.youtube.com/@GTM_now
Podcast directories: https://gtmnow.com/tag/podcast
The GTMnow Podcast - subscribe to support
It would mean the world to us if you subscribe to the show on your platform of choice. This helps support our growth, which in turn helps us continuously bring on bigger guests and deliver the content that you want to hear most.
The GTMnow Podcast tells the stories of how the top 1% of founders, operators, and investors build, scale and invest.
Each week, we uncover the pivotal moments, bold decisions, and go-to-market strategies that turn ideas into breakout companies.
GTMnow is the media brand of GTMfund - we are an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.
Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.
