If you dive deep into your Net Revenue Retention (NRR), Net Dollar Retention (NDR), expansion pipeline or closed upsell/cross-sells from last quarter, how much of this came from customers initiating these conversations versus your customer support or success (CS) team identifying the opportunity and driving the conversation?

For many Support and Success organizations, that ratio is lopsided. Account expansions happen to the team, not because of the team. Usually off the back of an amazing product or platform that happens to potentially address a customer’s challenge or solve a need. Maybe a customer asks for more licenses or coverage because they are a fast growing business, so the team processes it. Or maybe a customer mentions a new use case in a cadence call or ticket, and the team loops in sales. But the motion is reactive. In contrast to what could be a proactive, discovery-led approach where opportunity is identified off the back of consistently delivering a forward-thinking product roadmap paired with a consultative success or support outreach.

This isn’t the fault of the individuals on Support or Success teams, as most formed originally with the goal of providing post-sales support and ensuring value is delivered to customers against the outcomes they purchased the solution for. But this does fall on the leaders of these teams. As a Director, VP of Success, Support, Experience, or Chief Customer Officer- if you are not tying your team’s OKRs to revenue you’re unlikely to be able to justify your existing headcount or further team growth in CFO/Board-level conversations that require increased efficiency, increased automation, and clear ROI.

But what I’ve seen the past 12 years as a CS leader and team builder across multiple industries in logistics/supply chain, cybersecurity, and AI for customer experience- is the unique opportunity to evolve CS teams to align to revenue. But this all starts with answering the question “Have we delivered the outcomes we sold against?”. Regardless of the industry, or pre-sales process, when we sign a customer there is a promise made. And during the post-sales CX whether it’s through implementation, success, or support, everything needs to be centered around minimizing time to value delivery.

I’ve done this at multiple levels, startup, scale-up and high-growth enterprise organizations. Most notably as a founding CS leader at Darktrace, a leader in AI Cybersecurity for 5 years. I had the unique opportunity to accelerate our GRR, NRR, and NDR growth as we scaled from $200M to $1B in ARR as a private company, through an IPO, and later successful acquisition. This wouldn’t have been possible without building and elevating the CS team as the quarterback of the post-sales CX based on a core competency framework of product expertise, account/success planning, executive communication, stakeholder management, renewal rigor, upsell identification, customer advocacy, proactive engagement, best practice delivery, and cross-team collaboration.

As we scaled from 0 to 200 CSMs and 10,000+ customers (across SMB, Mid-Market, Enterprise) globally, executive and board-level leadership would not have allowed investment in building out this team without the critical focus on revenue capture.

Your People Need Technical, Commercial, and Executive Credibility

‍

Through interviewing thousands of CSMs, hiring, onboarding, developing segmentation, I learned first-hand the infinite number of ways organizations hire, run, and build their teams.

What was clear was that generic relationship management only gets you so far. During interviews as I scaled my team, if a CSM couldn’t demonstrate technical, commercial, or executive-level credibility in previous experience, or the ability to grow in these areas they were not a fit for my program. The strongest CSMs who had technical product expertise, could tie product to business outcomes, context switch from a day to day end-user to C-level, and have the growth-oriented mentality to uncover new use cases / opportunities- stood head and shoulders above the rest.

To find growth in existing accounts, your team needs relationship depth, technical product credibility, and executive alignment working together. If you build up these competencies in your CSMs, you’ll be able to own the relationship, drive optimization, deliver promised outcomes, and set the stage for new use case discovery that translates to additional revenue opportunities. If you only talk to an admin about day-to-day usage/issues/open tickets, you’ll never understand C-level client priorities. But vice-versa, if you don’t address the business outcomes your solution was procured to solve, then new use case expansion comes off as drive-by salesmanship.

Some organizations have the luxury of adding a post-sales Customer Success Engineer, Professional Services, or Consultancy type role that partners with CSMs in a 1:1 or pooled model. They can focus on prioritizing deployment or operational health reviews, proactive optimization, and increasing adoption well in advance for enterprise-level clients to ensure your solution becomes mission critical. Early hands-on execution that prevents downstream risk later in the customer journey.

At Darktrace we built an Analyst Consultancy program that did just that with deep security expertise. Starting out with Enterprise clients and later building out paid-for professional service models. At Forethought, we’re piloting an AI Value Architect role with one of our most technically-proficient CSMs that delivers short-term meaningful audits, optimization, and measurable increase in quantitative metrics like deflection, CSAT, resolution rate, minimizing time-to-value for new automation use cases.

But in a world where budgets are tighter than ever, and most CX leaders are being asked to handle an increased number of inquiries as their business grows, but head count remains flat, automation is critical. Every CCO wants to free up their CSM’s time to focus on more strategic alignment, stronger product experience and uncovering additional use cases and expansion.

But there are only so many balls CS teams can juggle at any given time. This is where Forethought can add significant value across the Customer Experience journey by saving CS and Support personnel time to focus on higher-value activities. What if rather than customers filing a support ticket or needing to engage in a conversation with their CSM for a question you’ve answered a thousand times, we could resolve this without ever needing a human’s eyes on it? Our AI agents can do this today via widget, email, voice, slack, across all channels. And you can connect this through MCP to any other AI solutions the rest of your business has built internally. What if you could proactively orchestrate a set of automatic processes at different stages of the customer journey? Or take all of the tribal knowledge, use case, and best practices that are stored in the heads of your top Enterprise CSMs- and deliver this at mass to your scaled/digital customers? Forethought’s Orchestrator, currently in beta, delivers this today with endless possibilities.

Build Predictable Expansion Into Your Process

By automating the routine tasks, building systems that can generate proactive triggers, you free up your CS team’s time to focus on the high impact parts of the job that include delivery against business outcomes, and uncovering new expansion opportunities that solve pain points.

Building a system that links product usage signals to expansion pipeline gives your CSMs a way to identify opportunities based on data instead of waiting for customers to raise their hand.

High adoption in one area combined with low usage in another often signals an opportunity. The customer is getting value, but they haven't discovered everything available to them.

"I had no idea Forethought did that" is a common reaction when CSMs actually walk customers through the depth of our full CX platform.

A CSQL (Customer Success Qualified Lead) program is another way to make expansion more intentional — and more predictable. Instead of relying on gut instinct, you equip your team with clear signals: usage patterns, accounts that match expansion criteria, and customers with similar use cases to ones you’ve already solved elsewhere in the platform. That structure gives CSMs a concrete reason to reach out, educate customers on what they’re missing, and proactively open conversations that drive meaningful growth.

Get Into the Room Where Budget Decisions Happen

If your CSMs only talk to the people who use your product day-to-day, you're probably not in the room where budget and expansion decisions get made. Building executive engagement into your account motion changes that. I’ve seen numerous situations where a CS team member was engaged daily with admin-level stakeholders via Slack, email, on cadence calls indicating an engaged customer- to then be shortly told they’re churning.

Regular practices like EBRs/QBRs and onsites should include stakeholders who control the budget. Digital executive pulse surveys or implementation surveys can give you visibility into decision-maker sentiment and activation roadblocks well before renewal conversations, so you're not caught off guard by concerns that have been building quietly. An ounce of prevention is worth a pound of cure early in the customer lifecycle.

At Forethought, for example, AI and CX have become board-level priorities, which means CTOs, CIOs, COOs, CCOs, and CEOs are increasingly involved in their AI CX solution evaluations. If technical leadership is evaluating whether to build AI capabilities in-house, we at Forethought always welcome the opportunity to be part of that conversation and can deliver immediate value through Headless Forethought.

When you already have the executive relationship, are delivering value, and have become critical infrastructure you're positioned as a strategic partner. When competition comes up or budgets get reviewed, you have the advantage.

Free Up Your CSMs for Strategic Work

Your CSMs can handle more strategic work if customers have other ways to learn your product and stay informed. Certification programs, technical webinars led by engineers, community office hours, digital email best practice tips are examples of educational content that could give customers a path to value that doesn't run through their CSM. Automated outreach like product announcements, quarterly CSAT reviews, and usage-triggered emails at different points in the customer lifecycle are examples of complementary digital touchpoints that could keep customers informed at scale.

At Forethought, for example, we launched what we call an AI Mastery Series—small, practical sessions targeting admins and power users, led by our implementation engineers and AI Value Architect with over 200+ attendees in each session. Customers have been asking for this kind of interactive enablement. We are also launching our Forethought Academy that will deliver on customers’ requests to self-serve their AI Support education through Forethought when it makes sense for them. That allows our CSMs more time to focus on strategic conversations, complex optimization, and expansion.

Stop Treating Retention and Expansion as Separate Jobs

Your CS team talks to your customers more than anyone else in your company. They know which accounts are thriving, which ones are frustrated, and which ones have needs they haven't articulated yet. That proximity is valuable—the question is whether your org is structured to turn it into growth, or whether your team is spending that access on maintenance.

The people best positioned to find expansion opportunities are the ones already in any given account, hearing about what's working, what's frustrating, and what's next. The same conversations that protect revenue can generate it if your team knows what to listen for and has the structure to act on it.

To see how Forethought helps CS teams move from reactive support resolution to driving measurable outcomes and strategic alignment with existing accounts using AI-driven automation, request a demo.

‍