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Breaking the Rules: What Happens When CS Enters Pre-Sales

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Breaking the Rules: What Happens When CS Enters Pre-Sales

It’s been about a year since I wrote about a discovery call, the one I wasn’t supposed to take, the $300K deal that changed the conversation, the proposal I was asked to write.

A lot has happened since then.

The proposal was approved. With caution, with questions, with “let’s try it and see what happens” energy. My manager and I worked through the operational concerns, including capacity planning, role clarity, and success metrics that span traditional boundaries. We got leadership buy-in to experiment with a different model.

And we’ve been running that experiment for twelve months now.

I need to share what we’re learning, because the results are challenging some fundamental assumptions about how customer-facing teams should work.

The Numbers

In the past year, I’ve been involved in 23 pre-sales engagements. Not as the AE. Not as the SE. As something we’re starting to call a “strategic value advisor,” we’re joining discovery calls, participating in solution design, and helping prospects envision their implementation journey before they become customers.

Of those 23 engagements:

  • 19 resulted in closed deals (83% close rate, compared to our typical 54%)
  • Average time to value decreased by 47%
  • Customer engagement scores in the first 90 days are 2.3x higher than those of customers who only met CS post-sale
  • Zero post-sale surprises or misalignment issues

But those numbers don’t capture what’s actually happening. Let me tell you about one deal in particular.

The Fortune 100 Story

Six months ago, we got pulled into conversations with a Fortune 100 company. Massive organization. Complex infrastructure. The kind of customer where deals typically take 18 months to close and another 18 months to fully implement.

They were evaluating Google Cloud for a significant product migration for mission-critical systems, high compliance requirements, and executive visibility at the C-suite level.

From the first call, we operated differently. Not just AE and SE, but what we’re now calling a “unified team”: AE handling commercial mechanics, SE architecting the technical solution, and me focusing on strategic value alignment and adoption planning.

Here’s what was different:

During Pre-Sales:

  • While the SE was working on technical architecture, I was identifying their Minimal Viable Business Outcome, the smallest deployment that would prove value the fastest.
  • While the AE was navigating legal and procurement, I was already building relationships with their implementation team.
  • While we were all presenting solutions, I was mapping their adoption journey and identifying potential friction points.

The result: Deal closed in 4 months instead of the expected 18.

But that’s not the interesting part.

Three Months to Full Adoption

The interesting part is what happened after the contract was signed.

There was no handoff. No “let me introduce you to your Customer Success Manager” moment. I was already supporting their onboarding. I’d been in the room since day one. I knew their business challenges, technical constraints, organizational politics, and definition of success.

We hit the ground running.

Week 1: We launched their pilot environment. Not in Week 4 after three onboarding calls and a kickoff meeting. Week 1. Because we’d already done that work during pre-sales.

Week 4: First business outcome delivered. They migrated a non-critical workload, proved the concept, and got executive buy-in for the next phase.

Week 8: Second phase deployed. Larger workload, more complexity, still ahead of schedule.

Week 12: Full production deployment of their major product. Live. In production. Mission-critical systems running on Google Cloud.

Three months from contract signature to full production deployment.

In our final strategic session (we’re calling these “Strategic Value Sessions” now, not QBRs—more on that in a moment), their CTO looked at the timeline and said something I’ll never forget:

“We’ve never worked this fast in the existence of our company.”

Why This Happened

I’ve been analyzing what made this different. It’s not that we got lucky. It’s not that this customer was uniquely easy to work with. (Trust me, Fortune 100 companies are never “easy.”)

It’s because we eliminated three massive sources of friction:

1. No Messy Handoffs

In traditional models, customers explain their business 3-4 times:

  • Once to the AE during discovery
  • Again, to the SE during solution design
  • Again, to implement during kickoff
  • Again to CS during onboarding

Each handoff introduces information loss, relationship reset, and delays.

We eliminated all of that. The customer explained their business once. To all of us. Together. And we maintained that context through every phase.

2. Onboarding Started Before the Sale

Here’s something radical we tried: We gave them access to a demo environment during pre-sales.

Not a generic demo. A customized environment configured for their use case. They could experiment, test, and explore before they signed anything.

By the time the contract closed, they’d already been using the product for six weeks. They weren’t starting onboarding. They were continuing it.

3. Strategic Alignment From Day One

The most significant delays in enterprise implementations don’t come from technical complexity. They come from misalignment: unclear success criteria, changing priorities, stakeholder confusion, and scope creep.

Because I was in the room from the beginning, we defined success together during the pre-sales process. We identified their Minimal Viable Business Outcome. We got executive alignment on what “winning” looked like.

When we started implementation, everyone was already rowing in the same direction.

What We’re Calling This

We don’t have official terminology yet, but we’re starting to use some language that feels right:

The Unified Team: AE + SE + CSM working together across the entire customer lifecycle, not in sequence but in parallel.

Minimal Viable Business Outcome (MVBO): The smallest deployment that delivers the most immediate value. Not the whole vision. Not the complete transformation. The one outcome that, if achieved quickly, gets everyone excited about what’s next.

Parallel Onboarding: Starting the adoption journey during pre-sales instead of after contract signature.

Strategic Value Sessions: Forward-looking partnership conversations focused on “what’s next,” rather than backward-looking QBRs that focus on “what happened.”

These concepts are still forming, but they’re becoming the foundation of how we operate.

The Pattern We’re Seeing

After a year of doing this, a clear pattern has emerged:

Traditional Model:

  1. Sales discovers and closes (3-18 months)
  2. Handoff to implementation (2-4 weeks delay)
  3. Kickoff and onboarding begin (8-16 weeks)
  4. Customer starts realizing value (12-24 months total)

Unified Team Model:

  1. Discovery with the whole team, MVBO identified (1-6 months)
  2. Parallel onboarding during pre-sales
  3. Contract closes, implementation continues seamlessly (no delay)
  4. Customer realizes value in first deployment (3-6 months total)

The unified model compresses timelines by 50-75% while simultaneously improving customer satisfaction and reducing churn risk.

What’s Working

After 23 engagements, here’s what consistently works:

Early MVBO Identification: Customers want to solve everything at once. Our job is to find the one outcome that proves value fastest. This becomes the North Star for both the sale and the implementation.

Demo Environments During Pre-Sales: Letting customers actually use the product before buying eliminates 90% of post-sale surprises and accelerates adoption dramatically.

Continuous Context: When the same team members are present from discovery through deployment, information doesn’t get lost, and relationships don’t reset.

Strategic vs. Operational Role Clarity: The AE handles commercial mechanics. The SE handles technical architecture. The CSM handles strategic value orchestration. When everyone stays in their lane but works toward shared goals, magic happens.

What We’re Still Figuring Out

This isn’t perfect yet. We’re still working through some challenges:

Capacity Planning: If CSMs are in pre-sales, how many existing customers can they support? The sweet spot is around 15-20 active customers with 3-5 pre-sales engagements simultaneously. But this is still evolving.

Compensation Structures: How do you compensate CSMs who impact both sales and retention? We’re experimenting with team-based bonuses tied to customer outcomes rather than individual quotas.

When to Engage: Not every deal needs CS involvement in pre-sales. We’re developing criteria for when this model makes sense (typically: enterprise deals, complex implementations, strategic customers, multi-year contracts).

Scaling Concerns: This model requires highly skilled CSMs who can operate strategically. How do we scale this without diluting quality? Still working on it.

What I’m Learning About Customer Success

This year has fundamentally shifted how I think about the role of Customer Success.

CS isn’t a post-sales function. It’s a customer lifecycle function.

Our job isn’t to manage customers after they buy. Our job is to orchestrate value at every stage of their journey—from the moment they’re considering a purchase through ongoing growth and expansion.

The “handoff” is the enemy of customer success.

Every time we transfer a customer from one team to another, we lose momentum, context, and trust. The best customer experiences are continuous, not sequential.

Speed to value is everything.

Customers don’t care about your product. They care about the outcomes your product enables. The faster we can help them achieve a meaningful business outcome, the more embedded we become in their operations.

Strategic partnership beats transactional service.

When customers view us as strategic partners who understand their business—not just vendors who sold them software—everything changes. They involve us in planning. They ask for our perspective. They think of us as an extension of their team.

An Invitation

If you’re in Customer Success and you’ve been pulled into pre-sales conversations, I want to hear from you:

  • What patterns are you seeing?
  • What’s working? What’s not?
  • How are you managing capacity?
  • What resistance are you encountering?

Because I think we’re onto something bigger than just “CSMs in discovery calls.”

I think we’re discovering a new operating model for how companies partner with customers.

And the organizations that figure this out first will have a massive competitive advantage.

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Chris Hood

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