John faced a similar situation on the sales side. When he arrived, growth had been driven entirely by the inbound PLG motion, with no outbound infrastructure, limited pipeline discipline, and disconnected GTM workstreams. He introduced a predictable pipeline engine, improved forecasting rigor, and fostered stronger collaboration across GTM functions.

Throughout these changes, the three leaders prioritized transparency and support for their teams. Jen found that true empathy meant having honest conversations early rather than avoiding difficult topics.

“Empathy means sharing feedback early, with care, and backing it with a plan,” she says. Her team created manager toolkits for candid performance conversations, established a predictable cadence of career check-ins, and tied clear expectations to business outcomes.

When managing large-scale organizational shifts, Jen, Jason, and John work closely to establish a change-communication pattern grounded in transparency: the why, what, when, and the support available. “Bringing on a lot of change can be jarring for teams,” says Jen. “We’re very thoughtful in establishing communication patterns that help teams feel more informed and connected about what’s happening across the company.”

2: Celebrate as one team, not as separate functions

Every leader knows the value of alignment – but teams need more than good intentions to make it happen. At Customer.io, it starts with shared accountability for outcomes.

Rather than splitting hairs over inbound, outbound, and partner contributions, John and Jason focus on total pipeline generated. While they monitor the individual components, they make it clear that the most important numbers to hit are the ones that they share.

They also celebrate publicly as one team. At their last Sales Kickoff, revenue leaders created distinct awards for Marketing partners, People partners, and Product partners, in addition to standard Sales awards – an important acknowledgment that achieving ARR goals is a team effort.

“Both John and I attend the weekly pipeline meetings because we want to signal to the GTM teams that we are equally committed to hitting that goal,” says Jason. The two leaders are also equally active in each other’s departmental Slack channels, regularly expressing praise for wins across functions.

John’s end-of-quarter posts on sales-led revenue performance always include a section on marketing’s contribution. Jason mirrors this in his posts on self-serve revenue, highlighting the work of the Account Management and Sales teams in driving upsells.

Behind the scenes, John and Jason launched a weekly pipeline generation council with shared targets. They appear together at events and meetings, celebrate wins as a unified team, and share responsibility for mistakes.

“We are obsessive about productivity metrics for both sales and marketing,” says John. “We set clear expectations with our people and hold them accountable.”

Jen adds that the team designs around outcomes first and lets structure follow. When discussing marketing operations placement, for example, they focus on what will drive the best results rather than protecting functional turf. They’re also transparent when discussing talent density within their functions, which enables open discussion during headcount and resourcing planning.

3: Drive AI adoption from the top – then fuel it from below

Customer.io has taken an all-in approach to AI, both within their product and as a productivity solution across every function. But the adoption didn’t happen organically – it required intentional leadership from the top and structural support throughout the organization.

Their CEO kick-started AI exploration with a company-wide memo outlining the importance AI would play for customers, the business, and employees. To move from memo to momentum, the C-team put several key mechanisms in place:

• A Slack channel called #ai-wins, where employees share how AI is improving their ability to do their jobs better and faster
• “Tiger teams" in departments like Engineering/Product/Design, and Marketing, to fuel experimentation and spread education quickly
• Broad access to budget and licenses for new tools, encouraging employees to experiment.

From a people perspective, Jen embedded AI adoption into key employee development stages: hiring, onboarding, development, and performance reviews. The team launched an internal AI Hub with starter guides, tool lists, and real internal case studies.

"We incorporated the assessment of personal AI adoption into our performance reviews,” says Jen. “This encourages regular conversations about AI between managers and their teams.”

4: Show up at the board with one story, one set of data

“Before anything goes to the CEO or the board, we make sure we’re on the same page — one story, one set of data, one clear message.” - John Schoenstein, CRO at Customer.io

Managing up effectively starts long before the board meeting. For John, Jason, and Jen, alignment begins months in advance through consistent collaborative touchpoints.

“Before anything goes to the CEO or the board, we make sure we’re on the same page — one story, one set of data, one clear message,” says John. “That unity builds a lot of trust.”

The team has built regular mechanisms to stay aligned:

• Weekly pipeline syncs and 1:1 meetings to hash out what’s happening in real time.
• Monthly financial updates where the C-team discusses performance and assesses what’s working and where they can improve.
• Quarterly business reviews with the broader executive team and their direct reports.
• Pre-board meeting prep sessions where they proactively surface tough questions.

“We are not aligning around the story in those two weeks before the board meeting,” says Jason. “It starts months before and gets refined through the collaborative touchpoints we’ve put in place.”

When they communicate upward, they focus on the “so what” — not just the numbers, but what they mean and what actions are being taken.

“The board doesn’t need every metric; they need clarity, confidence, and transparency,” says John. “Showing up as a cohesive team helps our CEO tell a clear story and shows that we’re aligned on both the challenges and the path forward.”

The team also uses board conversations as a two-way dialogue. Ahead of each meeting, they align on what insights they want to solicit that could help sharpen their own strategy. When shaping their AI adoption strategy, for example, they asked board members what they were seeing across their portfolios – how other companies were positioning AI with customers and structuring internal enablement.

“That outside perspective was incredibly valuable and helped us refine our enablement approach and narrative,” says Jen.

Wrapping Up: Quick takeaways for strengthening GTM alignment:

• From John: “Keep it simple. Focus on the fundamentals: clear comp plans, clean territories, and a consistent sales pitch. Simplicity creates clarity, and clarity creates alignment.”
• From Jason: “Seek out ways to celebrate the wins of your cross-functional partners in public settings. Once your teams see you do it regularly, they will start to mirror that behavior.”
• From Jen: “Design around outcomes first and let structure follow. Focus on how we win together – focus on what will actually drive results.”

This article was based on a panel discussion at the 2025 Spectrum Equity Sales & Marketing Leadership Summit, where GTM leaders from across the portfolio come together to share insights and best practices. Learn more about our portfolio companies and their leadership teams here.