CEO @ Alpha Presales | Teaching smart people to talk less and sell more. The smarter your sales engineers are, the more they need this.

I’m on LinkedIn to share stories and lessons from corporate sales training I do and sales kickoffs (SKOs) I speak at.

If you’re in Leadership, Sales, Pre-Sales, or Sales Enablement, you can follow me and get free value.

If you want to train your team to be better at Storytelling, check out Alpha GTM or Alpha Presales training.


--- HAPPY CUSTOMERS ---

✅ MongoDB (app dev)
✅ Optiv (cybersecurity)
✅ Exiger (supply chain / compliance)
✅ Paylocity (HR)
✅ Planful (finance)
✅ NICE (CcaaS)
✅ Eightfold (AI)
✅ OutSystems (dev tools)
✅ Keysight (manufacturing)
✅ Flexential (infrastructure)

--- RESULTS ---

“My sales rep doubled his number the quarter after you did training.”
— Ben, CEO, Iris

“I’m seeing more Alpha behavior happening. The SCs are stepping up in a bolder and more professional manner.”
— Jeff, Director of Solutions Consulting, Paylocity


--- HOW I CAN HELP YOU ---

• Sales Enablement - companies partner with us to supplement their in-house sales enablement. Storytelling is our most common training. We also have SKO workshops and are consistently ranked both #1 content and #1 speaker.

• Presales Leaders - SEs love Alpha Presales training because it’s specifically made for SEs. But most SE leaders don’t buy training for their SE team because they don’t have budget and are too proud to ask for help. If budget is your problem, just reach out. 90% of my clients don’t have budget and I help them get it. Your SEs deserve to feel appreciated and they don’t feel appreciated when your voice is the only one they hear from. 

• Sales Leaders - your sales reps don’t need another sales methodology. They just need to take control of the sale and stop doing whatever the client wants. Note: This doesn’t mean sales reps should be assholes. It means they should be leaders. That starts with the right process and right skills. 


P.S. I take all intro calls myself.  No sales pitch. We'll talk about what you want for your team, I'll tell you what we offer, and then if you think there's a fit, I’ll give you a quote or help you get budget for next year. 

Rew Dickinson

2025 Wrapped for Solutions Consultants!?

Pre-Sales SCs, SAs, SEs, what else?

Solutions Consulting (Presales) Wrapped 2025

What to do when a sales rep asks a solutions consultant to demo a feature that the customer doesn’t need (and how to handle it gracefully).

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Talks about #sales, #ventas, #presales, and #storytelling

CEO @ Alpha

I was asked: “How do you approach discovery calls before you have to give a demo?” Here’s a 5-part framework you can use for any discovery.

Where most sales reps and SEs mess up is they only ask questions about what the client is currently doing.

There’s not enough value in that.

This framework will help you go deeper. 

Time permitting, I dive deep into each one of the categories mentioned.

I may also ask:
- Was this your initiative or did it come down from above?
- What have you tried doing to fix it before?
- Is it already funded or do we need to help you get the budget and build a business case? 

There are many others that I go into in my Relentless Discovery workshops, but if you start here, you’ll be in good shape. 

If you like these videos you’ll like my newsletter more (read bio).

P.S. What other questions are you asking?

One of my clients just closed a $112,000 deal at a company with only 256 employees. Here's how. And no, it wasn't because of a slick demo by the SC. It was because of great discovery. 

Here's the full story...

The SC and AE were working an opportunity that you see all the time in complex sales: 

1. The prospect has a lot of problems, so they create a laundry list of features they need in their new solution. 

2. Then, the prospect gets so caught up in all the things they're trying to solve that they lose sight of what actually matters most to their business.

3. That's where most vendors mess things up. Most SCs would jump into demo mode. Show them everything. Click through every feature. Hope something sticks. 

Not this SC. 

Instead, he slowed down. Asked simple but powerful questions. Helped the prospect see what was REALLY important. 

Not just what they thought they needed, but what would actually move the needle for their business.

Afterward, the SC and AE devised a plan to meet the prospect's most pressing needs and FOCUS the conversations on those needs rather than on all the other "nice-to-haves." 

The result? 

A $112K win that one of the sales leaders called "flawless from start to finish."

Here's the lesson for AEs and SCs: 

You don't want your SCs to be demo jockeys. You want them to be strategic business partners who help prospects think clearly about their own business. To do that, you have to give them time to ask questions. 

The best discovery isn't about asking 47 MEDDPICC questions. It's about asking the FEW questions that help prospects figure out what's actually important.

When you do that, deals close themselves.

The Head of Sales at one of my clients told me this: 

"The only people on our team who tell stories are the people who have been at the company long enough to tell their own stories."

Yikes. 

It's 2025. 

Your people and your stories — not your products — are your differentiator. 

And don't even get me started on Sales Engineers, because most of us never tell stories, we just talk about the product. 


P.S. More content on storytelling coming: https://lnkd.in/eKaaGeZr. 
P.P.S. SKO workshops available for both Sales and SE Teams.

Every December 4th, I get flashbacks to high school, driving a beat-up Hyundai Elantra, listening to Jay-Z - The Black Album on cassette tape. 

Why December 4th? 

Because that's Jay-Z's birthday, and if you're like me, you can still hear Jay's mom, Gloria Carter, blasting through your speakers saying..."Shawn Carter was born December 4th..."

So this December 4th, I decided to drop a new album, "The Sales Album," modified, of course, by my career in sales.

---"December 4th"---

𝘛𝘩𝘦𝘺 𝘴𝘢𝘺 𝘵𝘩𝘦𝘺 𝘯𝘦𝘷𝘦𝘳 𝘳𝘦𝘢𝘭𝘭𝘺 𝘮𝘪𝘴𝘴 𝘴𝘢𝘭𝘦𝘴 𝘳𝘦𝘱𝘴 '𝘵𝘪𝘭 𝘸𝘦 𝘭𝘰𝘴𝘦 𝘰𝘳 𝘸𝘦 𝘨𝘰𝘯𝘦
𝘚𝘰 𝘰𝘯 𝘵𝘩𝘢𝘵 𝘯𝘰𝘵𝘦 𝘐'𝘮 𝘭𝘦𝘢𝘷𝘪𝘯 𝘢𝘧𝘵𝘦𝘳 𝘵𝘩𝘪𝘴 𝘥𝘦𝘢𝘭'𝘴 𝘱𝘢𝘱𝘦𝘳𝘸𝘰𝘳𝘬𝘴 𝘥𝘳𝘢𝘸𝘯

𝘚𝘦𝘦 𝘺𝘰𝘶 𝘢𝘪𝘯'𝘵 𝘨𝘰𝘵𝘵𝘢 𝘧𝘦𝘦𝘭 𝘯𝘰 𝘸𝘢𝘺 𝘢𝘣𝘰𝘶𝘵 𝘴𝘢𝘭𝘦𝘴 𝘳𝘦𝘱𝘴 𝘴𝘰 𝘭𝘰𝘯𝘨
𝘈𝘵 𝘭𝘦𝘢𝘴𝘵 𝘭𝘦𝘵 𝘮𝘦 𝘵𝘦𝘭𝘭 𝘺𝘰𝘶 𝘸𝘩𝘺 𝘐'𝘮 𝘵𝘩𝘪𝘴 𝘸𝘢𝘺, 𝘩𝘰𝘭𝘥 𝘰𝘯

𝘐 𝘸𝘢𝘴 𝘤𝘰𝘯𝘤𝘦𝘪𝘷𝘦𝘥 𝘣𝘺 𝘢 𝘴𝘢𝘭𝘦𝘴 𝘤𝘰𝘮𝘱 𝘱𝘭𝘢𝘯 𝘵𝘩𝘢𝘵 𝘥𝘰𝘯'𝘵 𝘷𝘢𝘭𝘶𝘦 𝘮𝘦
𝘞𝘩𝘰 𝘮𝘢𝘥𝘦 𝘮𝘦 𝘤𝘢𝘳𝘦 𝘭𝘦𝘴𝘴 𝘢𝘣𝘰𝘶𝘵 𝘳𝘦𝘯𝘦𝘸𝘢𝘭𝘴, 𝘺𝘰𝘶 𝘴𝘦𝘦 

𝘞𝘩𝘪𝘤𝘩 𝘮𝘢𝘬𝘦𝘴 𝘮𝘦, 𝘢 𝘮𝘰𝘳𝘦 𝘴𝘪𝘤𝘬𝘦𝘳 𝘈𝘌, 𝘢𝘯𝘥 𝘮𝘺 𝘣𝘰𝘴𝘴 𝘸𝘰𝘶𝘭𝘥 𝘤𝘭𝘢𝘪𝘮
𝘈𝘵 𝘵𝘦𝘯 𝘥𝘦𝘢𝘭𝘴 𝘭𝘢𝘴𝘵 𝘲𝘶𝘢𝘳𝘵𝘦𝘳 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘨𝘪𝘷𝘦 𝘩𝘦𝘳 𝘯𝘰 𝘱𝘢𝘪𝘯

𝘈𝘭𝘵𝘩𝘰𝘶𝘨𝘩 𝘵𝘩𝘳𝘰𝘶𝘨𝘩 𝘵𝘩𝘦 𝘺𝘦𝘢𝘳𝘴 𝘐 𝘨𝘢𝘷𝘦 𝘩𝘦𝘳 𝘩𝘦𝘳 𝘧𝘢𝘪𝘳 𝘴𝘩𝘢𝘳𝘦
𝘐 𝘨𝘢𝘷𝘦 𝘩𝘦𝘳 𝘩𝘦𝘳 𝘧𝘪𝘳𝘴𝘵 𝘳𝘦𝘢𝘭 𝘴𝘤𝘢𝘳𝘦, 𝘐 𝘮𝘢𝘥𝘦 𝘲𝘶𝘰𝘵𝘢 𝘪𝘯 𝘋𝘦𝘤𝘦𝘮𝘣𝘦𝘳 𝘳𝘪𝘨𝘩𝘵 𝘵𝘩𝘦𝘳𝘦. 

𝘚𝘩𝘦 𝘬𝘯𝘰𝘸𝘴 𝘮𝘺 𝘱𝘶𝘳𝘱𝘰𝘴𝘦 𝘸𝘢𝘴 𝘰𝘯 𝘱𝘶𝘳𝘱𝘰𝘴𝘦, 𝘐 𝘢𝘪𝘯'𝘵 𝘱𝘦𝘳𝘧𝘦𝘤𝘵, 𝘐 𝘤𝘢𝘳𝘦
𝘉𝘶𝘵 𝘐 𝘧𝘦𝘦𝘭 𝘸𝘰𝘳𝘵𝘩𝘭𝘦𝘴𝘴 𝘤𝘢𝘶𝘴𝘦 𝘮𝘺 𝘤𝘰𝘮𝘱 𝘱𝘭𝘢𝘯 𝘸𝘢𝘴𝘯'𝘵 𝘮𝘢𝘵𝘤𝘩𝘪𝘯 𝘮𝘺 𝘺𝘦𝘢𝘳

𝘕𝘰𝘸 𝘐'𝘮 𝘫𝘶𝘴𝘵 𝘴𝘤𝘳𝘢𝘵𝘤𝘩𝘪𝘯 𝘵𝘩𝘦 𝘴𝘶𝘳𝘧𝘢𝘤𝘦 𝘤𝘢𝘶𝘴𝘦 𝘸𝘩𝘢𝘵'𝘴 𝘣𝘶𝘳𝘪𝘦𝘥 𝘶𝘯𝘥𝘦𝘳 𝘵𝘩𝘦𝘳𝘦
𝘞𝘢𝘴 𝘢 𝘱𝘦𝘳𝘴𝘰𝘯 𝘵𝘰𝘳𝘯 𝘢𝘱𝘢𝘳𝘵 𝘰𝘯𝘤𝘦 𝘩𝘪𝘴 𝘵𝘦𝘳𝘳𝘪𝘵𝘰𝘳𝘺 𝘥𝘪𝘴𝘢𝘱𝘱𝘦𝘢𝘳𝘦𝘥

𝘐 𝘸𝘦𝘯𝘵 𝘵𝘰 𝘸𝘰𝘳𝘬, 𝘨𝘰𝘵 𝘨𝘰𝘰𝘥 𝘥𝘦𝘢𝘭𝘴, 𝘤𝘰𝘶𝘭𝘥 𝘣𝘦𝘩𝘢𝘷𝘦 𝘸𝘩𝘦𝘯 𝘐 𝘸𝘢𝘯𝘵𝘦𝘥
𝘉𝘶𝘵 𝘐 𝘩𝘢𝘥 𝘥𝘦𝘢𝘭 𝘥𝘦𝘴𝘬 𝘥𝘦𝘦𝘱 𝘪𝘯𝘴𝘪𝘥𝘦 𝘵𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘴𝘵𝘰𝘱 𝘥𝘦𝘢𝘭𝘴 𝘸𝘩𝘦𝘯 𝘤𝘰𝘯𝘧𝘳𝘰𝘯𝘵𝘦𝘥

𝘏𝘰𝘭𝘥 𝘰𝘯...

---

What would you add to verse 2? 

What were you listening to on the way to high school? 


P.S. Get my monthly newsletter for presales and sales teams (SEs, AEs, and Sales Leaders): https://lnkd.in/eKaaGeZr

No alternative text description for this image

I didn't have a Black Friday deal, so I decided to make one up. $500 to whoever does this...

---
The Problem: 

There is someone at your company who is planning your SKO. It's brutal. Think wedding planning. But worse. Tons of product updates, strategic initiatives, and speakers who will be drinking the night before. Rough. 

The Solution: 

I'm speaking at 4 SKOs in January. There are 2 ways I help companies with this: 

1. Interactive Keynote Sessions - I give you a 45-90 minute banger of a session where the sales team is learning a new skill like storytelling, working together, and competing. It's a nice alternative to lectures and fireside chats from people who have never done sales before. 

2. Team Sales Workshops - you work together as a team and learn Storytelling, Storytelling for Discovery, Presales, or Client Leadership skills that help you take control of the sale and win. 

How You Can Help: 

If you send this to your SKO planning team and book me for SKO, I will give you one of those big fat checks for $500.00 to thank you for making the intro. I'm here to help. 

P.S. What do you think of ChatGPT's rendition of me holding a $500 check? It doesn't seem to listen very well, does it?

A sales leader just told me that her team does a good job of upfront discovery, but doesn't do rediscovery throughout the sales process. Here's why that's a problem and what to do about it...

Imagine you're on a first date. 

Are you going to tell the person all of your dirty secrets? 

Probably not. 

But on the 2nd, 3rd, 4th, 5th, date you would reveal more and more info because you trust the person more. 

The same principle applies to B2B sales. 

As you build trust, people will tell you more information. 

That's good because you can solve their problem better and faster. 

Hence why rediscovery is a good idea. 

It's okay to ask the same questions. 

You'll get different answers. 

Discovery never ends.

300,000 vs 3.

It takes about 300,000 minutes of doing enterprise sales to get halfway decent at enterprise sales. At that point, you might actually feel comfortable managing an enterprise sales cycle. 

It takes less than 3 minutes to make your prospect feel seen, heard, and understood. 

If you skip the 3 minutes, you wasted the 300,000.

Every person in sales has done it... the prospect is talking, and we're thinking about what we're going to say next. But did you know that only 7% of our communication is the words we say? The other 93% is non-verbal. This post will help you with the other 93% so you can be a more effective communicator. 

---

In my sales training courses, we talk a lot about non-verbal communication and confidence. 

I use this game to demonstrate the value of confidence. Save this post and play the game in your weekly team meeting or SKO breakout. 

---

The game is called "Expert Panel." 

It will help you with the 93% of communication that isn't your words. 

How to Play:

1. Pick 3 volunteers to be experts. One expert will give "good" advice, one will give "bad" advice, and one will give "REALLY BAD" advice. 

2. Give the experts a topic to talk about (e.g., “The best way to get rich quick", "How to get through airport security the fastest", "Tips for losing 15 pounds in 15 days", etc.)

3. One at a time, each expert delivers a 60-second monologue with total and complete confidence. It doesn't matter if you are telling the truth or lies, you must speak CONFIDENTLY. 

4. Each expert can build on or contradict what came before.

5. Keep the tone serious, even when the content is absurd.

6. Afterwards, the team votes on which expert appeared most credible based on tone and body language (not words). 

The game is valuable for salespeople because most of us focus so much on our words that we forget what we're saying with our tone and presence.

Have fun with it.

People buy confidence.

Want to master sales skills? Don't buy one of my Sales Kickoff (SKO) workshops. It's a waste of $15,000 -> $50,000. Do this instead...

If you want to master a skill, you can't do it by sitting through one SKO session. 

You need a SYSTEM. 

For example, this is the system I use with most of my B2B sales clients, like Sitecore, Paylocity, and Flexential, when they want to master a skill like storytelling: 

-1- BEFORE SKO: We train the managers to use the Alpha Storytelling Methodology
-2- AT SKO: We train the individual contributors
-3- AFTER SKO: We give managers the support materials they need, and we do follow-up training with the team to build the storytelling muscle

The truth is, if you're losing deals, it's rarely because your product isn't good enough. 

It's usually because you got outsold and your story isn't good enough. 


What do you think? Do you talk about your product too much? 


P.S. Forward this to your enablement/planning team. Even if Alpha isn't the right fit, the before/during/after system is worth considering for any skill you want your team to actually adopt.

Sales: "What do you do if you don't have enough time to cover everything in a meeting/demo?" 

This is a tough situation to be in, but the solution is to ask questions and listen. Here are the 3 questions I would ask, and why. 

---

1. What would make this meeting/demo a success for you? 

-> Why: Because if you don't ask this, you don't know what your client is looking for. You're merely guessing.

---

2. I'm confident that we can deliver everything you're looking for, but if you could only get ONE thing, what would it be and why? 

-> Why: Because if you don't ask this, you waste time talking about things that aren't that important to your client. 

---

3. How are you going to decide between the different options that are available to you?

-> Why: Because if you don't ask this, you have no idea how the client is going to evaluate you. It's like taking a graduate course and not knowing which is most important: the homework, attendance, or the final exam. 

---

When I'm short on time in a sales meeting/demo, I start here. 

Usually, the best thing you can do in sales is listen. 

What would you do?

Most Sales Kickoff content is horrible. 3 hours of corporate lectures. 4 hours of product sessions. 150+ people staring at their phones. Utter failure. It should have been a webinar. Not an SKO...

I'm on a mission to help you make the most of the 1 time of year when you have your whole sales team together at SKO. Try this game during your SKO breakout session to help your team have fun and get better at Discovery. 


---


The game is called "Discovery Speed Dating." 

The problem it solves is this: 

Most AEs and SEs go through the same discovery questions for every meeting and make zero attempt to personalize their discovery to the audience. That's why your prospects hate doing discovery. They feel like the discovery is for the seller, not for them. 

This game helps you tailor your discovery to your audience so they feel seen, heard, and understood.

How to Play:

1. Choose the top two roles that your team sees in sales meetings (e.g. VP of Supply Chain, IT Manager, Controller, etc.)

2. Put people into groups of two. Each person will play the seller twice and the buyer twice.

3. Do four rounds of mock discovery, practicing tailoring to the buyer roles you identified in Step 1. 

Rd 1: PersonA interviews BuyerRole1
Rd 2: PersonB interviews BuyerRole2
Rd 3: PersonA interviews BuyerRole2
Rd 4: PersonB interviews BuyerRole1

Before you start, ask yourself, "What is something unique about this person's role that I can acknowledge to get them to know that I understand them?" 

Then say that thing that makes their role unique and watch them let their guard down and tell you their problems. 

Remember, you're not doing discovery for you, you're doing it for THEM. You're the doctor. THEY are the ones with the problem. 

---

In B2B sales, your product isn't your differentiator, your sales team is.

We just wrapped up a week of virtual training with Netwrix, and what a team!
Average tenure: 7.5 years! Highly technical. Former security professionals who know their stuff inside and out.

Normally, deeply technical SEs struggle with storytelling. But not this group! They were packed with great stories, we just had to surface them.

I knew that this group was special because I watched their sales calls beforehand and I saw guys like Dakota already telling stories without even realizing it. The raw material was there. 

Here's how we unlocked it:
- Alpha Storytelling Methodology and playbook
- Guided instruction + group activities
- Focus on translating 7.5+ years of technical expertise into client value

What makes an SE team valuable isn't technical acumen alone. It's their ability to communicate that acumen in a way that gets clients to see value and take action. This team can do both. 

Thank you, Ian and team, for investing in your people and making sure your SEs' voices are heard.

THIS is Solutions Engineering.

P.S. If you want to get better at storytelling and other professional sales skills join the Alpha GTM newsletter where we publish valuable free content once a month: https://lnkd.in/eKaaGeZr

We had Bob Ross join us for sales training last week. Can you spot him (her)?

The hardest part about being a virtual (high velocity) Solutions Consulting team is that you usually don’t get to sit in on discovery calls.

That’s why most SCs in this situation would just talk about their product the whole time. 

Not this team!

They’re pros- they did such a great job of setting the table before jumping into the demo, getting the prospect to open up about their needs, telling stories, doing discovery on the fly, and closing things out with clear value to the customer. 

In fact, after our training the SC leader got a note from one of the sales reps telling her how amazing Bob Ross’s demo was! 

Keep up the great work team!

We play this game in my sales training workshops because most people are too busy thinking about what THEY'RE going to say instead of LISTENING to the CLIENT. 

This game trains you to listen. It's great for Sales Reps, SEs, and Managers to play. Save this and play it as an icebreaker in your weekly team meeting or SKO breakout. 

---

The game is called "1 word story." (Clever, I know)

How to Play:

1. Create teams of 3-5 players.

2. Someone will start telling a story by saying ONE word only.

3. The next person adds ONE word to the story. 

4. Each player continues the story, adding only ONE word. 

NOTE: Only add words that make sense for the story!

The game is hard because you can't think about what you want to say next, you have to just listen. It's also hard because you will get the urge to add more than one word and control the story. You can't do that either. 

This game teaches us to do what all great salespeople do– listen.

All of my clients want to know how my other clients are using AI. Here's one way. Steal this How To so you can personalize your solution to your audience and stand out in a sea of vendors who all sound the same. 

P.S. I'm heading to NYC today to listen to a panel discussion by Austin Meyer at OpenAI, Ryan Lempa at Figma, Jeff Black at Gong, and the Sales Engineers of New York (SENY). I'll do another post on what I learn from them.

---

How to use AI to personalize your solution to your audience and stand out: 

Let's say you're selling a Financial Planning software platform. You likely sell to multiple industries, including Retailers, Manufacturers, Insurance companies and others.

So even though you're selling the same solution, how it is used by your customers is completely different. 

For example, a Retailer like Starbucks operates 30,000+ stores and has to do financial planning around leases, real estate, and everything else. 

But an Insurance company like Progressive doesn't have to do any of that. They have to worry about actuaries, risk, and pricing policies. 

So you could be selling/demoing the exact same Financial Planning solution to them, but how you personalize the value to them should be completely different (but most people don't do this). 

Most sales reps and sales engineers don't think about this because they're experts in their product, not experts in their customer's industry. 

That's where you can use AI to help you. 

Go to your favorite AI and ask this question: 

"I'm selling [Product] to [Industry], what is unique about how they do [What Your Product Helps With] that other industries don't have to deal with?"

Here's a real example I put into ChatGPT: 
"I'm selling Oracle to an Insurance company, what is unique about how they do Financial Planning that other industries don't have to deal with?"

Then you turn that response into a question to learn more about the customer's business in your meeting with them: 

Here's an example question for selling to an insurance company:
"The financial planning process is different for insurance than it is for most companies because you have to integrate actuarial forecasts and other things, so can you help me understand a little more about the nuances of how your team brings all of that together today?”

Then listen. Learn. Figure out how you can help, because that's what sales is all about. 

How are you using AI?

We play this game in my sales training courses. The problem it solves is that most salespeople are too busy thinking about what they're going to say next that they don't listen. You can't do that in this game, you have to listen. Save this and play it in your weekly team meeting or SKO breakout. 

---

The game is called "Alphabet Story" (Clever, I know)

How to Play:

1. Create groups of 3-8 people.

2. Tell a story, but each new line must start with the next letter of the alphabet. 

Example: 

Person 1: “A dragon appeared in the break room.”
Person 2: “But nobody seemed surprised.”
Person 3: “Clearly, this happens every Monday.”
...

Keep going through the alphabet — if someone gets stuck, the group helps out.

The game is helpful because it teaches you to do what all great salespeople do– listen.

2025 Wrapped?! Sorry Salespeople, we still have a month left to go.

What did we miss on your 2025 wrapped?

2025 Wrapped for Salespeople

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.

James Kaikis

This year, I lost a deal because I insisted on doing discovery before a demo. That is when I realized something really was dying: No Disco, No Demo.

Hear me out before you bring your pitchforks to the conversation.

I've recited this line so many times in my career. 
And, in an AI-first world, I don't believe it applies like it once did. 

For many SEs, discovery is designed to uncover pain points so you can tailor the demo.
But today?
You can learn more about your customer before you ever speak to them.

And they can learn way more about you, too - so they EXPECT MORE. 

They don't want to be interrogated for 30m just to "earn" a generic demo. 
They expect you to show up already knowing their world, their language, and their priorities. 

Discovery ABSOLUTELY still matters. But the old way of discovery doesn't. 

Here is how to modernize your GTM motion: 

- Do AI-powered research before you meet. 
Ask ChatGPT about the company's strategic priorities, projects, and challenges. If they're public, it's all out there. If private, you can still piece it together.

- Research every attendee. 
Use GPT to look up what they post, care about, and drive inside the org. 
Upload your company's value prop to ChatGPT and ask 
"What value statement would resonate most with each person on this call?"

- Talk to the front lines.
Reach out to ICs and FLMs via LinkedIn.
Ask how they're currently handling the problem you solve.
(And if you have budget, throw them $5 coffee gift card for their time). 

- Set expectations early. 
Email each attendee before the call and ask, "What would make this meeting a win for you?"
Even if only one person replies, you've set a different tone - consultative, not transactional. 

So, "No Disco, No Demo" isn't dead. 
But it is no longer a hard line. 

And if you're in transactional sales thinking, "I don't have time for this", I am here to tell you it can all be automated. 

I have used this approach over the past year, and customers have told me, "You know more about my business than I do." 

Is "No Disco, No Demo" outdated? How are you adapting to this new world? 

(PS - I break down this at the 12m mark in my keynote "The Future of GTM is Customer-Focused & AI-Powered" if you want to dig deeper)

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.

For most of my career, I’ve said the same thing: “If it’s not a live demo, it doesn’t count.”

Then I saw something in London that completely flipped my perspective.

At DemoFest, the team from Consensus and Trupeer AI ran what I can only describe as a simulation of the future of demos.

The presenter spoke into his computer while the crowd made chaos - shouting, clapping, total background noise (see video). 

The system listened, cleaned the audio in real time, and turned that same delivery into a crisp, studio-quality version.

Then it automatically generated a German version, with the presenter’s same tone and energy.

That moment broke something for me.

I used to believe that the “live” part of a demo was the gold standard because it proved authenticity, confidence, and control.

But what buyers actually want isn’t live.

They want proof.

They want to see themselves in the product.

Their workflow. Their environment. Their language. Their reality.

It’s about making the product come alive for the buyer, wherever and however they engage. 

We talk a lot about “buyer enablement” in SaaS - what I saw in that room was buyer immersion.

And it made me realize:

Maybe the best demo isn’t "live" - the outcome is what really matters.

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.

Warren Buffett just wrote his last shareholder letter - and he used it to talk more about character than capitalism.

On November 10, Buffett released what he says will be his final annual letter to Berkshire Hathaway shareholders. The closing section, “A Few Final Thoughts,” reads less like an investor update and more like a handbook for leaders.

Here are the top takeaways for leaders:

- “Envy and greed walk hand in hand.”

He points out how easy it is, especially at the top, to measure yourself by what other CEOs have.
In tech, it’s not just compensation. It’s valuations, rounds, titles, followers, stage time, press.

If envy is steering your decisions, you’re already off course.


- “Don’t beat yourself up over past mistakes- learn from them and move on. It is never too late to improve.”

Mistakes are guaranteed. Growth is optional.

For founders and execs, the real question isn’t: “Did you get it right?”
It’s: “Did you learn from your mistakes?”

And that last line - “it is never too late to improve” - calls out any leader running from the accountability of change.


- “Kindness is costless but also priceless.”

Greatness, in his framing, isn’t net worth, headlines, or power.
It’s how you treat people in thousands of small interactions, most of which will never be public.

In a world obsessed with frameworks and strategy decks, he still points back to something simple: how you show up for other humans.


- “Decide what you would like your obituary to say and live the life to deserve it.”

Not your next round.
Not your next promotion.
Not your next valuation.

Your obituary.
That’s a very different scoreboard than the one most of us optimize for.


There’s something powerful about a leader at the very top, looking back over a lifetime of compounding…

…and choosing to focus on envy, growth, kindness, and legacy instead of performance metrics.

He closes with one last piece of guidance:

“Choose your heroes very carefully and then emulate them. You will never be perfect, but you can always be better.”

That’s not investment advice; it’s a values-based operating system for leaders.

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?

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

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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James Kaikis

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