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

I run Alpha GTM – our mission is to help you sell more without being "salesy." 

Prior to this, I did: Engineering -> Consulting -> Presales -> Sales. 

I've trained thousands of sales leaders, reps, and SEs from 23 different countries. Through my training, I've learned that the best sales professionals are not successful because they "sell" – they're successful because they lead. 

That's why we teach Leadership. 

If you follow my content, you'll get playbooks to help you and your team master Leadership, Discovery, and Storytelling so you can sell more effectively. Be a Leader. Own the sale.

Rew Dickinson

Every Sales Engineer who joins a company should hear these words from their manager on Day 1: 

1. I don't expect you to have all the answers
2. I don't expect you to be right all the time
3. I don't expect you to be perfect

I DO expect you to: 

1. Do your best.
2. Get better every day.
3. Listen more than you talk.
4. Ask questions even if you feel nervous.
5. If you don’t know the answers, get them. 

We set this unrealistic expectation that SEs are supposed to know all the answers, and when they don't they feel awkward. 

That's why most of them try to control the meeting by talking the entire time. 

What'd I miss?

CEO | Professional selling without being “salesy”

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Founder

Sales + Sales Engineering

Consulting + Software Engineering

Financial Analyst

Helping CROs and CSOs run a predictable GTM

My average sales cycle was 4.5 months. My company's average was 9. I always used 2 documents to help me do this: 1 you've probably heard of, and 1 you probably haven't. I teach both in my sales workshops. Here's why they matter and how to do them: 

The Problem: 

Most clients think the best way to evaluate software is to: 
1. Look at the generic stuff that Gartner publishes -> 
2. Line up 5 potential vendors -> 
3. Get demos from all of them-> 
4. Realize they all look the same -> 
5. Downselect to 2 vendors -> 
6. Do a bakeoff -> 
7. Realize that they forgot to include their actual workflows in the bakeoff ->
8. Do a follow-up POC to close the loop on their remaining questions -> 
9. Get ready to make a decision -> 
10. Realize that some person from Enterprise Architecture, Security or IT has to do something ->
11. Start engaging legal at the very end of the evaluation -> 
12. Get delayed 4 weeks...because...lawyers -> 
13. Finally, sign a contract. 

It's like thinking that the best way to drive from Seattle to LA is through New York. 

It's absurd, but most clients don't know that because most clients have never bought your product before and don't know how to do it. 

That's why in all my sales workshops, I teach the team how to create a Visual Evaluation Plan (VEP).

NOTE: This is not a Mutual Action Plan. Mutual Action Plans are amazing when the client already likes you, but they're far too detailed for early-stage prospects where you're not the vendor of choice (yet). 

To create your VEP, do this:
1. Map out the slowest sales cycles you've been through
2. Map out the fastest sales cycles you've been through
3. Visually draw what the fastest sales cycles looked like in a way workflow that you could present to a customer. 

Then show the VEP to the client and say, "We've worked with [numberOfCustomers] customers and found that the fastest and most efficient way to get through an evaluation is to follow this process. How does this compare to what you had planned?"

Nearly every time I do this, the client thanks me. 

It gives them a plan. 

Be a Leader.

If you're in Sales or Sales Engineering, your job is not to convince. Early in my career, I thought it was. Here's what I learned (plus, why the best AEs and SEs are rarely the most convincing)...

---

I was the SE on one of the biggest accounts in my company's history ($48 million). We needed the Retail Group, the Financial Advisory Group, and three other groups to all agree that our solution was the right one.

Earlier in my career, I would have focused on giving the most compelling demos and POCs to all these groups. That works, to a degree. But once I got more mature in sales, I realized that the most powerful thing you can do in a sales cycle isn't to convince or persuade the person in front of you – it's to coach them. 

For example, I found out that one of the Solutions Architects that we were selling to had worked for 3 out of the 5 groups that we needed to get onboard. 

So rather than try to convince him, I decided to coach him. The client had asked us to do a POC, but I set up a workshop with the Solutions Architect where I taught him how to build out a workflow completely on his own. 

I would do this often because I've found that when people build something, it's way easier for them to present it to their peers. 

For example, have you ever tried to give a presentation that someone else built? It's miserable. You're nervous the whole time because you didn't build it yourself. 

Once this Solutions Architect built the solution, he owned it. Then he went around to the four other business groups and showed them what he built.

He became my internal seller. I didn't try to convince him, I coached him instead.

When you convince people, you're not equipping them to convince anyone else. But when you give them what they need to sell internally, they can sell when you're not in the room.

Every time I'm working a deal now, I'm asking myself: "How do I turn the people I'm selling to into my internal sellers?"

Stop convincing. Start coaching.

I watch 100 sales presentations a year. And almost everyone gets this wrong. They try to "sell value" by talking about the product. But the value isn't in the product. It's in the prospect. Watch this to see where "value" actually comes from and how to sell a lot more of it.

If your sales reps are giving demos, you have a MASSIVE problem. Your sales reps should be building pipeline. Your sales engineers (SEs) should be progressing pipeline. If that's not happening, these are 5 of the most common reasons why (and 5 solutions).


NOTE: For deals under $10K and demos under 10 minutes, it's fine for sales reps to do demos. This post is about enterprise sales, not transactional sales.

---

PROBLEM 1: It takes too long for a sales rep to get an SE assigned to them.

SOLUTION: There's no reason it should take two weeks for an SE to be assigned to a deal. Could you imagine walking into a car dealership and them telling you that you can test-drive a car in two weeks? That's absurd, and you'll lose before you even get a chance to demo. Fix your assignment process or hire more SEs.


PROBLEM 2: Your sales reps think they can give better demos than their SEs. 

SOLUTION: Sometimes sales reps are better at demos than SEs. In fact, I was an example of that because I used to be an SE and could give great demos. But if you're selling mid-market or enterprise software, and you're giving demos yourself, you look bush league. What message do you think you're sending to a prospect that you're the only showing up to a meeting with them? Don't do it. A lawyer can represent themselves in court. That doesn't mean they should.


PROBLEM 3: Your sales reps want to control the narrative and are afraid of what the SE might say.

SOLUTION: I see this a lot. SEs are super smart and super detail-oriented but they haven't mastered SALES skills. Nothing drives a sales rep crazier than an SE who knows 17 ways to do something and gives the customer 17 options. All that does is create indecision. SEs: Your job isn't to give the customer options. Your job is to help the customer make a decision.


PROBLEM 4: Your SEs aren't that good at sales, so sales reps don't want to bring them into the deal.

SOLUTION: Just because you hire sales engineers with social skills doesn't mean they're good at SALES. You need to TEACH them SALES skills. In this order: Leadership - > Discovery - > Storytelling. That's how they "sell" without being "salesy." If you don't teach them these skills, they will forever be seen as "technical resources." Either develop your own SE training curriculum or get an SE-specific training curriculum like Alpha Presales.


PROBLEM 5: Your Sales reps don't actually know how to use SEs.

SOLUTION: I also see this a lot. Sales reps think that SEs are there to give demos. They don't realize that your SE (not your product) IS your differentiator. When I was a sales rep, I would bring my SE into the deal early because I learned that clients would tell them way more than they would ever tell me. That helped me uncover more pain and sell more value. Your SEs are your secret weapon.


Bottom Line:
If your sales reps are giving demos, it means they aren't building pipeline, which is the most important thing they can be doing.

What would you add?

This sales meeting started horribly. The sales rep briefed the SC on the opportunity 2 minutes before the prospect joined the call. Somehow, they pulled off a miracle together, largely because the SC was an absolute beast with 10 years of experience and knew how to lead. 

Here are 3 things that the SC did that show just how valuable SCs can be in sales: 

1- The SC got the prospect talking early. Notice how he peppered in questions early on. This got the prospect talking and sharing problems, so that when he demoed, he was aligning to those problems, not talking about features. 

2- About halfway through the demo, the prospect started to "sell herself." The SC recognized this, stopped demoing, and immediately pivoted to a businses conversation to help her build her business case. He "sold" less and started asking questions again. 

3- Toward the end of the meeting, the SC went from "selling" to "leading." He talked about how expensive it is for people in her role to engage outside consultants for help with things they could figure out themselves with the right software. Then he asked her how often she has to go to consultants for answers and she revealed how often and how much it costs. It immediately justified the investment.

This is an incredible example of SC leadership in a deal. 

Sales Reps: prep your SCs before the call. 
SCs: don't just demo, be a leader.

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3 years ago, I was on vacation in Hawaii, and someone asked me what I do for a living...

I said, "Have you ever talked to an engineer and had no idea what they were talking about?" 

They laughed and said, "Yes, all the time!"

I said, "I train engineers to communicate in ways that normal people can understand."

Then someone from the back of my tour bus said, jokingly, "Do you work with scientists?"

I laughed and said, "No, but I could!"

That was a funny joke...

Or was it? 

What started out as a joke 3 years ago actually became a reality this year. 

I recently had the privilege of working with Revvity Signals' Field Application Scientist (Presales) team. 

These folks are ACTUAL SCIENTISTS!!! They're the smartest people I have ever worked with. But my favorite part is that they're also some of the most empathetic people I've worked with. 

In this picture, we were going through the Alpha Presales soft skills training, and everyone was leaning in, learning, and having a blast doing it. 

So if there's anyone out there who thinks that us techies don't have soft skills, we do, we just prioritize truth first. 

Thank you, Matt, Ismail, and Jinsoo for allowing me the privilege of working with your team.

Last month, I did an SKO where several sales reps in the crowd would chime in and add their 2 cents to the discussion. 

Afterwards, one of the Solutions Consultants (SCs) pulled me aside and asked me, "How do you speak up in a big group like that?" 

I asked him, "What makes you think that you can't?" 

We chatted for a bit, and I ultimately told him this: 

Many SCs are afraid to speak up at SKOs or in big groups. Sometimes it's because they feel like the event is for the sales reps, and sometimes it's just because they're nervous speaking in a large group. 

Either way, remember this: 

1. It is quite often that SCs have MORE experience than sales reps at the company. For example, the average SC tenure tends to be 3-7 years at a company, whereas the average AE tenure is only about 18 months. 

2. If you have something valuable to share with the team, you don't have to wait for your turn to share it. You're on the sales team, too. You can contribute whenever you want. 

SCs have a voice. Don't be afraid to use it.

This was a really bad demo. I watch hundreds of them a year, and these 3 problems come up again and again. Here's how to fix them. 

---

PROBLEM 1: "Teaching," instead of communicating value.

In my training, I teach the Alpha AAA Framework (Audience, Annoyance, Afterward). Before you jump into a feature/solution, always know the Audience, their Annoyance, and what their life would look like After your solution is in place. If you don't know that, you're just selling features, not value. 

PROBLEM 2: Talking too much.

Breathe. 11 minutes and 19 seconds is way too long for anyone to listen to a demo. Simple tip: plan out your questions before you demo. For every solution you plan to show, write at least 1 question to ask before or after you show it. 

PROBLEM 3: Reacting, not leading.

Both sales reps and SCs mess this up. They're trying to be nice, so they offer more information. I can't tell you how many times I hear meetings end with..."We're happy to dive deeper into any of these things." Rarely do prospects need more information, they usually just need to build a business case. Help them with that. 

What other problems do you see?

This was one of the best things I've ever heard a Sales Leader say...

I was in Dallas, TX, with Motorola, and we were teaching storytelling to the Solutions Consulting team. 

That's when the SVP of Sales, Jeremy Smith chimed in and asked the SCs...

“Do you know where we can get these customer stories from?“

The team responded:
- "Marketing!"
- "Our website!"
- "The CS team!"

Jeremy said, "yes, yes, and yes."

But then he said the best answer of all...

“Go meet with the customer directly. You can go on-site. You don't have to ask your sales rep for permission."

I loved this because there are so many SC teams that I talk to who feel like they work FOR their sales reps – You don't. 

You have every right to do what's right for your customer.

Be you.

Sr VP Resilience & Security Sales | Business Continuity, Security Ops & Emergency Management

Salespeople: Your tone says everything. So if you're, 
- Starting the meeting by apologizing for giving the corporate deck, or
- Racing to get through the corporate deck, or
- Telling people "I only a few slides..."

Stop. 

If giving the corporate deck is valuable for the customer, then don't apologize for doing it. 

If it's not, then skip it.

2 years ago, Todd Janzen and I sat down and talked about 2 massive problems in B2B sales: 
1) Sales Reps take too long to be productive (because B2B sales are super complex)
2) Sales Engineers don't have the capacity to be on every demo

These are still massive problems. 

Demo automation helps with both of them because: 

1) It gives your sales reps the content they need to be productive on Day 1
2) It increases the capacity of the SE team, while also putting SEs into the pipeline conversation as revenue drivers

If you're not following Todd and Consensus, you ought to be.

We're hiring a video editor at Alpha Presales!

But first, who this is NOT for...

If your portfolio is full of walk-and-talk, "day-in-my-life" influencer cuts, this isn't for you. Nothing wrong with that work. It's just not what we do.

We're not building a personal brand for the algorithm. We're building a resource for PROFESSIONAL Presales and Sales people. 

Leaders. SCs. Sales reps. Anyone trying to get better at their craft.

They don't need sizzle. They need substance.

---

What we care about:

- Clean, educational content that respects the viewer's time
- Structure that makes complex ideas easy to follow
- Quality over virality, every time
- An editor who gets that the content IS the product

My personal mission is to provide the best, most valuable content for presales and sales professionals and maximize value per second of watch time. 

Steak. Not sizzle. 

---

If you've edited training content, webinars, or professional how-to videos and you take pride in making ideas land we'd love to see your work.

Apply below, or share this so we can find the right person!

This is a behind-the-scenes look at what I do when a company asks me to run their sales kickoff (SKO). 

Lesson for all sales enablement professionals -> if you want people to remember what you teach them at SKO: 

1- Make people compete as a team (not just listen to a lecture)
2- Reinforce the training after SKO

P.S. What has been your most memorable SKO ever?

I get this question all the time in my sales training: “What do you do when people are quiet and you’re not getting much engagement in your demo?” 

When I hear this, I often ask the person, “what makes you think the quiet people aren’t engaged?”

That usually gets people thinking...

As sellers, we can’t assume that being quiet means people aren’t engaged. 

I’ve sold software and trained salespeople all over the world and there are largely two dynamics at play: 
1. Culture
2. Behavior

For example, Nordic countries are quieter than Southern European countries. New York is very different from Iowa. And Australia is different from Japan. 

On top of that, you have behavior. For example, I’m a verbal processor and I tend to get clarity through speaking. So you will hear me speak during meetings. That has nothing to do with being an American. 

On the other hand, my training director, who is also American is an internal processor and she prefers to think privately first before verbalizing her thoughts. 

So if you can’t assume quiet means disengaged, what do you actually do about it?

1. Set expectations in the beginning: tell the audience upfront that you've built in time for questions throughout, and that you'll be asking them things along the way.

2. Plan your questions in advance: for example, after showing a new solution, ask an open-ended question like, “How does this compare to how you’re currently doing things?” The key is asking HOW, not closed-ended questions like “would this be helpful for your team?” (Yes/No). 

3. Give people something to confirm or correct, for example, you can say something like, “most customers are either looking to increase conversion rate, or they’re trying to get better control over their forecast, which is it for you?” They’ll either confirm one or the other, or correct you and tell you something completely different. 

Don’t assume that quiet means disengaged. But don’t get lazy and just talk the whole time.

When they say your job is to "sell." If only they knew what it takes...

What's worse: 
1. "Umm"
2. "Uhh"
3. "Right?"
4. "Ya know."

Fire away!

If you're sending me a cold email, don't apologize or say "sorry" in it. 

If you're doing it right, I'm the one with the problem, not you. 

I should be thanking you, not vice versa. 

You're the doctor, not me. 

Help me.

That's the mindset. If you don't have it, you're not selling, you're begging.

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

Over the past 7 days, I’ve used Claude Code to build two meaningful apps that are saving my business at least a dozen hours a week.

A week ago, I thought I was fairly well-versed in what these models could do.

I’ve done the research.
I routinely speak with builders.
I was hands-on six months ago in my last role.

Like many people, I understood the story around this AI shift.

What I didn’t understand was what it feels like to actually build something yourself that would have cost $15,000 and taken three months, and instead turn it around in 10 hours for $100 in credits.

I haven’t run a SQL query in 10 years.

The biggest realization wasn’t the cost or even the time savings. It was that I didn’t need engineers to do it.

I didn’t need to translate what I wanted, and hope it came back correctly.

I could build it myself.

And the quality is real. The team is already using it.

That shift changed how I see my own capability. I realized I am capable of far more than I was operating at. As a result, my business is immediately stronger and more dangerous because of that new leverage.

The gap between idea and execution just collapsed.

If you’re a CEO, an operator, or early in your career, you need to block time and get hands-on with this to understand what is possible.

There are leaders quietly building right now.

The playing field is level for the moment.

It won’t stay that way.

This week has been one of THOSE WEEKS! The highs are so high with the official launch of SolutionExec, the announcement of our Off the Record conference, and face to face interactions with some of my favorite people. 

After our Virtual Kickoff, I jumped on a plane to Atlanta to work with David Maloof on our newest Enablement programs. 

But what started out as just a working session turned into an action packed day. 

Thanks to Justin McDonald and Melissa Mandel for meeting us at lunch AND giving us a tour of the Saleo office. It was about time I was able to take a picture in front of that logo at the entrance! We appreciate your partnership and dedication to moving the profession forward. 

What are the chances that Yuji Higashi and Mattie Stremic are also in Atlanta to host a dinner?! Thank you to Better Career for allowing me to join the dinner to have great conversations, see old friends, and make new friends. 

It was great to see Akash Ganapathi of Opine and meet Alec Wnuk of Navattic. Also, thank you for sponsoring the Better Career dinner and allowing me to join!  

As I wait to board my plane back to Chicago, I’m ending the week on a very high note. 

✌️ 🤙 

PS - We’re bringing 100 SolutionExecs together for an Executive-only conference, 'Off the Record,' in NYC on April 15th. If you’re interested in being part of the conversation, let’s talk!

I've been asked several times: What is SolutionExec, and how do I get value out of it?

To answer that question, we have to acknowledge that the Solutions profession is changing faster than most leaders are prepared for.

Longer sales cycles.
Tighter budgets.
More accountability for revenue and retention.
Decreased headcount.
Blurred lines between Sales, Solutions, and Customer Success.

This is a structural shift, and SolutionExec is our response. We exist to equip SolutionExecs with the private network, resourcing, and executive programming to lead the next era of go-to-market.

On March 4th, we are hosting our Virtual Kickoff (https://lnkd.in/gA72RCJe). 

After months and months of working behind the scenes, we are looking forward to sharing our roadmap.

You’ll hear directly from CROs, Chief Solutions Officers, and Global VPs of Solutions who are navigating this market right now.

We’ll walk through what we are building, why it matters, and how it applies to you and your team.

If you are leading in this profession today, be in the room.

Register now.

200 Executives in one room discussing How to Win in Hard Markets. Count me in!

GTMshift is teaming up with The Transaction and Jorge Soto to bring you Learn from Legends, a deep dive into the brightest minds in GTM. 

You’ll hear from: 
- Cristina Cordova 
- Chris Degnan 
- Scott Albro 

And a few surprise guests that you do not want to miss!  

Shout out to our partners: LinkedIn, FullEnrich, UserGems 💎, Avarra, and Captivate Talent for making this event possible!  

Sign up now. https://luma.com/w6x2lgd9

Alright LinkedIn - I’d like to open a discussion on a hot topic: the distinction between Forward Deployed Engineers (FDEs) and Solutions Consultants (SCs).

If your business utilizes both roles, I am interested in understanding where you define the boundaries for each.

Specifically, I want to hear your perspectives on the following:

- Collaboration: In what areas do these roles complement each other, and where do you typically see them conflict?
- Career progression: How do these roles evolve? Are FDEs promoted into SC positions (or vice versa), or are they entirely separate career tracks? 
- Hiring and skill requirements: When you're recruiting for these roles, what are the non-negotiable skills or backgrounds for each?

From the many private conversations I’ve had, it seems there is a lack of industry consistency on this subject. I could ask another 20 questions but we can start here. 

Let's talk.

What Does SaaS Crash Actually Mean for Solutions Leaders? The GTM org is being redrawn. Here's why Solutions leaders who move now will define what comes next.

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Open article: Everybody’s Talking About the SaaS Crash. Here’s What It Means for Solutions Leaders by James Kaikis • 8 min read

Everybody’s Talking About the SaaS Crash. Here’s What It Means for Solutions Leaders

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