Preparing CROs & CEOs for the future of B2B SaaS | GTMshift | CRO Functional Head @ Pavilion | Former CRO | Co-Founder @ PreSales Collective (Acquired) | Breaking The GTM Playbook |

I’ve always been fascinated by what makes a great customer experience—not just good, but truly memorable. My interest piqued while working in hospitality at Hyatt, where I learned how small details could turn a routine interaction into something special. 

That same obsession led me to tech, where I learned to scale exceptional experiences across sales and GTM teams at Showpad and Salesforce.

Then in 2020, I saw an even bigger opportunity—the need for a real community in PreSales. So I built one.

The PreSales Collective started as a simple idea and grew into a global movement with 35,000+ members, four business lines, and a full-time team dedicated to elevating the profession. In 2021, it was acquired, a milestone that cemented just how powerful community can be in shaping an industry.

Now, at TestBox, I’m taking that same passion for innovation and connection and applying it to how businesses evaluate software. The B2B buying experience is broken: endless sales cycles, generic demos, and a lack of real hands-on experience before making a decision. TestBox is changing that by enabling buyers to test-drive software in live, pre-configured environments before they buy, leading to better, faster, and more confident decisions. 

We’re redefining the way companies purchase technology, making the process easier, more transparent, and built for today’s fast-moving GTM teams.

Outside of work, you’ll find me traveling, hunting for the best new restaurant, or diving into a new challenge—whether it’s fitness, an unfamiliar experience, or a tough problem that needs solving. I believe the best insights come from staying curious and never getting too comfortable, and that’s how I approach everything I do.

I’m trading my basement and Zoom tiles for real rooms with real peers, working through challenges that never show up on LinkedIn.

Over the past few weeks, I’ve been sitting with some of the most brilliant minds in our profession, talking about what actually matters:
- the pressure executives are under
- the tradeoffs they’re making
- the reality of their business, without the spin 

Across every conversation, the theme was the same:
- pipeline is harder
- scrutiny is higher
- Executives are being asked to do more with less clarity than ever.

- Jeff Margolese and I spent an entire day planning for the biggest thing to hit the solutions profession since March 2020. 
- Spoke at ☁️ Cliff Simon AI Road Show about the wins I saw building AI-first GTM in my last role (and enjoyed a great dinner that evening). 
- Made fast new friends in Eric Gilpin, Ben Dietz, and Jen Allen-Knuth; looking forward to launching Dawg Assembly at the Autobahn Country Club in 2026. Also, thanks Steve Davis for always looking out for me and inviting me. 💪
- Finally spent more than a few minutes with Leslie Venetz! Nothing beats a signed copy of her book with a motivational quote. 
- Breakfast with the NorthShore-ish crew. Peter Turim, Paul Cushman, and Daniel Frailey. Sorry to miss you Jared Gibson. 
- Watching Benjamin Fleishman and Paul Anderson continue to shine in their careers. I hired both of them at Showpad and their growth trajectory has been so impressive.
- Met and had a fascinating convo with AI expert Pablo Landa.Thanks for the introduction Jody Geiger.  

These conversations are feeding a clearer, simpler, more customer-focused blueprint for GTM teams feeling this pressure. I’ll walk through what that looks like in an upcoming newsletter.

James Kaikis

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If you ask me how I’m doing, I’m thriving, thankful, and fulfilled - that’s what matters in life. 

Over the past two weeks I’ve had the opportunity to mix personal and professional.

From celebrating my wedding anniversary with my wonderful wife to a college reunion where I haven’t seen friends in 10-15 years!

To catch uping with professional friends at CRO events in the city. 

And even hosting my brother for a multi day working session. Add in hosting my cousins and watching the Steelers play the Bears (rough loss). 

PS - haven’t been on a golf course in 10 years but I’m picking it back up in 2026. Business on the course? I’m in.

If I had to lead or build a Solutions Engineering startup team, here's the EXACT roadmap I would follow.

I've spent 10 years building and scaling SE teams. 

And I've learned that what separates great teams from mediocre ones isn't talent, it's the foundation you build from day one.

Most leaders get this wrong. 

They take too long to hire, onboard slowly, and never develop a strong bench. They react instead of lead.

Here's the step-by-step roadmap:

Phase 1: Listening Tour
Start by listening - to your solutions team, sales org, marketing, customer success, product, and engineering.
Understand what the org is known for. Where do SEs add value? Where do people wish they had more SE support? Where are the bottlenecks? (Because there always are.)
You need to know who you are and who you aren't. Identify your top talent and the people who get shit done.

Phase 2: Build a Culture of Innovation 
Challenge the status quo. Start thinking about where you can change things.
I have a saying: I micromanage process, not people.
This is where you add new processes to improve efficiency. Create a culture of innovation and calculated risk-taking. Find early wins to showcase something different.

Phase 3: Bleed Outside Your Box
Where can you make a greater impact on sales? On customer success?
Where and how can you deliver more value beyond your traditional role?
This is how you justify more headcount and comp plan changes, by proving expanded impact.

Phase 4: Measure the Impact
Where and how have you implemented new changes?
How has it impacted sales cycles? Upsells? Expansions?
Measure everything. Use data to prove your value and fund your next phase of growth.

Phase 5: Market Leadership 
Build clear career paths with meaningful enablement.
Want to attract A-players? Show them exactly how they grow from SE → Senior SE → Principal SE → Solutions Leader (if they want to be in leadership).

Make it concrete, not aspirational.

Elevate your team's expertise to keep pace with changing customer expectations. 

Your buyers are smarter and more informed than ever; they want consultative partners who understand their business.

The SE role isn't what it used to be, and neither are customer expectations.
Build with that reality in mind.

What would you add to this roadmap?

(PS - picture of some of the Showpad SE team in 2019 at SKO in New Orleans)

Want to be the Solutions Engineer every Account Executive fights to get on their deals? Or the “AI expert” everyone Slacks when they’re stuck and need a better way?

This December, David Maloof and I are running a 3-day AI-Powered Solutions Engineer workshop for SEs and Solutions Leaders who want to actually put AI to work in their day-to-day.

We’re focused on three outcomes:
- Adopting an AI Mindset: understanding the tools landscape and Prompting 101 (without the hype)
- Research, Discovery & Demo Prep: using AI to do the unglamorous work faster and sharper
- Demo Presentation & Storytelling: turning AI research into clear, compelling customer narratives

If you’re an SE/SC who wants to apply AI to real workflows to get ahead, or a Solutions Leader who wants a clearer playbook for how your team can leverage AI to become more effective, this is for you.

We’re keeping it intentionally small and hands-on.

👉 Grab your spot via the link in the comments.

PS - use your L&D budget for this workshop. If you need a justification letter, let me know.

AI isn’t replacing Solutions Engineers. It’s widening the gap between elite SEs and everyone else.

Most Solutions Engineers I talk to aren’t worried about AI taking their job.

They’re worried about falling behind the SEs who learn to adopt AI first.

And they should be.

Because there’s a real shift happening in the SE world right now that no one wants to say out loud:

The SE who learns AI now becomes the SE every AE wants on their deals.

Not because they’re technical geniuses.
Not because they’re the loudest in team meetings.

But because they can do the work faster, sharper, and with more customer context than everyone else.

I’m seeing it everywhere:

- The SE who turns messy notes into a clean POV in minutes
- The SE who builds tighter demos because they started with better research
- The SE whose stories land because they’re backed by insights

Here’s the uncomfortable truth:

AI won’t replace SEs.
But SEs who use AI will absolutely outpace the ones who don’t.

This isn’t about “prompt engineering.”
This isn’t about being an AI influencer.

It’s about working differently.

Faster cycles.
Better preparation.
Clearer narratives.

More time spent on winning the deal… not wrestling with internal docs or reinventing the wheel before every call.

SEs who embrace this are already separating themselves from the pack.
And leaders who build these workflows into their teams aren’t just “experimenting with AI”... they’re creating a performance gap that’s going to widen fast.

The reality?

AI is the new leverage layer in Solutions Engineering.
And the people who understand how to wield it are going to be the ones everyone else leans on.

If you or your team want to become AI-Powered Solutions Engineers, let's talk!

What separates good GTM teams from elite ones? The speed of their feedback loops. For a CRO, that speed looks like:

- Feedback happens in real time, not at the end of the quarter
- Coaching layered into the next call, not a week later watching game tape
- Messaging and talk tracks are evolving daily, not once a quarter

I’ve been rebuilding the GTMshift narrative lately.
Not in a vacuum, but through fast, low-risk at-bats inside of Avarra.

No need to pressure-test new messaging or positioning in front of a customer; I can pitch Coach Cate using real-life scenarios until the story is sharp.

One thing keeps proving true:
Great teams don’t out-message the competition.
They out-iterate them.

If your team gets one rep a week and your competitors get five, you know who improves faster.

How quickly does feedback reach your reps after a key call?
Hours? Days? Weeks?

The future of Solutions Engineering isn’t more technical.
It is more influential. But why? 

AI is giving SEs the time back to shine in front of customers.

Executives keep telling me the same thing in every room I’m in.

Pipeline is tighter. Scrutiny is higher. Teams are expected to do more with less clarity than ever.

That pressure is landing directly on Solutions Engineering, who are already overworked and burnt out.

And the SEs who lean into AI are separating themselves fast.

Here’s what I’m seeing across the teams that are winning right now:
1. Research becomes seconds, not hours.
Teams are turning raw company data into buyer insight in minutes. Sharper discovery. Better narratives. More relevant demos.

2. Messaging becomes clearer.
Buyers don’t remember features. They remember the story.
AI is helping SEs refine the flow, simplify the value, and translate complexity into language stakeholders actually understand.

3. Focus goes back to influence, not admin.
Recaps. RFP drafts. Meeting notes. Follow ups.
When AI handles the busy work, SEs spend time shaping the deal instead of cleaning up behind it.

This is the shift.

Technical depth still matters.

But clarity closes. Speed wins. And the buyer remembers who helped them make sense of the journey.

If you want to build these skills the right way, we’re teaching them live in the AI Powered Solutions Engineer cohort.

We focus on the techniques that actually move deals.
- Research
- Discovery
- Demo storytelling
- Deal influence

If you’re feeling the pressure in your role, this is the moment to upskill.

Join David Maloof, Jody Geiger, and me as we spend three days helping you become the AI-Powered Solutions Engineer.

More information on the workshop here: https://lnkd.in/gBub8nvS

My family finally knows what I do... “You work in AI, right? My ChatGPT is acting funny. Can you help?” 😅😂😭🙄

Multiple people asked me last week if I really bought 30k Full Enrich credits just to test the product.

I did.

If I am going to put my name on something, I need to use it first.
Not a demo. Not a one-pager.
Real usage. Real data. Real scenarios.

That is how I approach every brand partnership.
I only partner with companies whose products show up in my actual work, not just my feed.

With FullEnrich, the value showed up quickly.

Before agreeing to anything, I ran it through three real tests:

✅ Volume test: I pushed it through thousands of records to see how it handled messy, inconsistent, mixed-source data.

✅ Accuracy test: I validated outputs across multiple providers to see which gaps got filled and how often.

✅ Workflow test: I called a friend who is using it at their business to walk me through their workflows and talk through the end output.

That is where the waterfall enrichment approach clicked for me.
Clean, complete, automatically stitched data without manual fixes or heavy lifting.

I burned through more than 25k of my 30k credits because I needed to be confident in real-world performance, not theoretical value.

That is why I partnered with them.
Not because of an offer.
Not because of a campaign.
Because the product earned its way into the work.

For me, that is the standard.
Use the product. Prove the value.
Then decide if the partnership makes sense.

Trust is built that way.
And trust is the only thing that scales.

#FullEnrichPartner

The gap between AI-first teams and everyone else is getting wider every day.

I've been talking to GTM leaders who've completely rebuilt how their teams operate around AI.

They're not using AI for incremental productivity gains. 
They're redesigning entire workflows from scratch.

Most teams are asking: "How can AI make this task 10% faster?"

The teams pulling ahead are asking: "Where can AI be a multiplier for my team? How do we empower our people to do better work?" 

They're redesigning for 10% productivity gains at the organizational level by using AI to augment human capabilities, not replace them.

Here’s the pattern I'm seeing:
Traditional approach: Use AI to write better emails, summarize calls, and generate reports.

AI-first approach: Redesign the entire customer lifecycle around value-added touchpoints. 

What this looks like in the GTM motion:
↳ Marketing teams generating 10x more content with the same headcount 
↳ Sales teams work more opportunities through automated workflows 
↳ Solutions teams are delivering more personalized demos without as much prep work

The difference isn't the tools. It's the ambition.

Most teams are happy that AI saves them 30 minutes a day.

AI-first teams are asking: "What becomes possible if AI handles 60% of this workflow?"

To put this in perspective: AI workflows can cost less than $1 to complete research tasks that would cost $100+ if done manually by humans.

That difference creates a massive gap in execution velocity.

The shift required:
↳ Don't think "AI assists my team" - think "My team orchestrates AI" 
↳ Don't think "AI makes us faster" - think "AI enables the impossible" 
↳ Don't think "AI improves our process" - think "What if we rebuilt this with AI from day one?"

The GTM teams that figure this out first will have a compound advantage. 
They'll move faster, cover more ground, and deliver better experiences with the same resources.

The ones that don't will keep optimizing yesterday's workflows while the market moves on.

Are you using AI to work faster, or are you redesigning how work gets done?

When asked what motivates me, it is my achiever mindset. More importantly, it is the desire for significance. 

These are two of my top Gallup Strengths, which I discussed on the Lodestar Podcast with ☁️ Cliff Simon of Polaris Ops. 

As defined by Gallup Strengths, Significance is "a desire to be important, recognized, and to make a lasting impact. Individuals with this theme want to work on meaningful projects that allow them to stand out and achieve goals with a significant, lasting legacy. This drive fuels their independence, professional credibility, and ability to inspire others by highlighting the impact of everyone's work."

So when people ask why do I do what I do? 

Simply to make an impact, as there is nothing that is more professionally fulfilling.

Check out my episode in the comments.

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