Building Your Enterprise CS Framework: From Strategy to Scale Part 3

Stakeholder Alignment And Managing The Relationships That Matter

Author

Tomas
April 23rd, 2025

Featured Article

Welcome to Part 3 of 7 on enterprise CS. Moving on from last week’s convo about onboarding – now lets look at how to manage and influence your stakeholders.

If your stakeholders aren’t aligned, your implementation is already dead.

It doesn’t matter how good things are going on your team if you don’t have buy-in from the people who hold the keys. Enterprise buyers are full of competing priorities.

Here’s how to get them on the same page – that is, on your page. 

Misalignment means failure

The latest numbers show that 62% of implementations flop because teams ignore the key influencers.

If you wanna make sure that’s not you and your crew – here’s where to start:

1. Figure out exactly who the major players are. 

  • Decision-makers (Who signs checks?)

  • Saboteurs (Who’s clinging to legacy tools?)

  • Silent Allies (Who’s quietly rooting for you?)

2. Keep close tabs. Assign someone (usually an Account CSM) to own the relationships. Ask them to meet KPIs like:

  • 5+ face-to-face meetings per stakeholder/month

  • 100% awareness of your customer’s departmental KPIs

The more you know, the better you can influence. For example, let’s say you figure out the CFO is obsessed with month-end close time. Great – now you can tailor every update to that metric.

What happens when stakeholders bolt (Trust me, it happens. A lot.)

A single exec departure can derail 6 months of work. 

First, try to stave off that happening by:

  • Track your stakeholders: Capture their goals, pet peeves, and preferred metrics. Update it quarterly.

  • Leverage insider allies: That mid-level HR manager who loves your product? Let them by your inside eyes and ears.

And if you get a new exec, be sure to get them on your side – fast.

  • Rebuild rapport in 72 hours: Prep a demo right away showing how you’re solving the new leader’s public pain point (e.g. cloud migration delays)

  • Demonstrate your value to them specifically:  New CFO? Send a 3-slide deck showing how your tool cuts their top 3 costs.

Don’t assume a steady team. Stay in the loop, and keep thinking one step ahead.

Don’t be gentle. Do what you have to to force alignment. 

Enterprise departments butt heads sometimes. OK, actually they butt heads a lot. In my experience, a passive approach never works. Address things head on and get yourself right in the middle of things.

Phase 1: Host a kickoff meeting.

  • Like I recommended with onboarding strategy, make sure you get everyone in the same room. IT, Finance, HR, and Ops – get them to agree on a single priority with you at the centre of the solution. 

  • Remember: Don’t let them leave without signed success metrics.

Phase 2: Make strategic updates.

  • Send tailored recaps by departments:

    • IT: “SSO integration: 2 days ahead of schedule.”

    • Finance: “Your AP team saved 200 hours last month.”

    • HR: “83% of employees completed training.”

  • Tie everything back to the unified goal:

    • Let’s say everyone wanted to see operational cost reduction. Find a way to link every deliverable to that KPI.

Train CSMs to speak C-Suite

CSMs talk features – but Most CSMs talk features. But what stakeholders need to hear is revenue, earnings, and impact. 

Start building in better comms by:

  • Hiring people who get it: Ask candidates: “How would our tool impact a client’s P&L?” Take on the ones who can answer it.

  • Tie promotions to metrics: Think: “Our client reduced payroll costs by $X using our tool.”

  • Arm your CSMs: Show them how to connect the analytics with specific stakeholder goals. 

Bottom line? Don’t lead with a product roadmap – lead with the client’s priorities.

The game plan from here

  1. Identify your major players: List every stakeholder for your top account. Highlight who actually controls budgets.

  2. Host a 30-minute “Alignment Sprint”: Force the key department heads to agree on one shared KPI.

  3. Get your CSMs thinking from a stakeholder point of view: Give a bonus to whoever can best articulate a client’s EBITDA story this month. 

Remember that implementation success depends on stakeholder alignment. If they’re a mess – you’ll be fighting battles every step of the way. Get everyone together, find the common thread, then keep them focused on that central driver. 

P.S. Next week, we’re cracking into technical integrations and nailing data migrations.


Tomas

Events

Save The Date

TSIA World INTERACT 2025
📅 Date: April 29–May 1, 2025
📍 Location: Orlando World Center Marriott, Orlando, FL, USA
🌐 Website: https://www.tsia.com/conference​

SaaStr Annual 2025
📅 Date: May 13–15, 2025
📍 Location: San Mateo Event Center, San Francisco Bay Area, CA, USA
🌐 Website: https://www.saastrannual.com/​

14th Annual Customer Experience Strategies Summit
📅 Date: May 28–29, 2025
📍 Location: Sheraton Centre Toronto Hotel, Toronto, ON, Canada
🌐 Website: https://www.customerexperiencecanada.com/​

Deep Dive

What We've Been Reading

What We've Been Listening Too