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

CEO | Professional selling without being “salesy”

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?

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.

Just wrapped up Sales Kickoff with Planful in Palm Springs, CA. This was my 8th SKO of the year, and Planful did the opposite of what most companies do at SKO...

They spent almost all their time focused on their customer – not their product, not their positioning, not their competitors. 

In fact, we did two sessions focused on the most important thing (OUR CUSTOMER): 

1. Customer Value Discovery
We did a 2-hour, deep, hands-on session on how to discover what customers actually need, not just what we want to sell.

2. Knowing our Customer and Owning the Sale
We did a 2-hour interactive workshop where we broke down each industry and the buyers Planful serves, to help guide them through the sales process more efficiently. 

I love working with sales leaders like Steve who are more focused on their customers than anything else, because that mindset shows up in everything they do.

Thank you, Steve, Mel, John, Emily, Ben, Andrew, and Ameesh, for finally getting to meet this team in person!

P.S. Not a bad place for SKO, huh?

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Founder

Sales + Sales Engineering

Consulting + Software Engineering

Financial Analyst

Helping CROs and CSOs run a predictable GTM

Planful

SVP Sales

CEO @ Alpha GTM

In my SE training, I always ask how many SEs have heard of the 3 Whys. Less than 50% of SEs raise their hand. Here’s why that matters for SE teams and how to apply the 3 Whys in Sales Engineering. 

---

The 3 Whys are the 3 questions that a prospect needs to answer if you’re going to sell anything to them: 

- Why do anything? 
- Why do it now? 
- Why do something with this vendor? 

Until the prospect has mentally answered these 3 questions, they’ll never buy. 

The problem is that most SEs give demos that only answer one question for the prospect: 

- Why do something with this vendor? 

They leave out the 2 more important questions: 
- Why do anything? 
- Why do it now? 

This is why SC discovery is so critical. 

We can’t just give demos and talk. We have to ask questions and tell stories, because those things help customers answer: 
- Why do anything? 
- Why do it now? 

For example, if you sell an expense management solution and a client tells you that they have a manual process for doing expenses, you don’t jump right into the demo. 

Instead, you say, “How long have you been dealing with this?”

They’ll probably say, “It has been like this forever.” 

That’s when you say, “Is it getting better or worse?”

They’ll probably say, “It’s getting worse because we’re trying to do more face-to-face meetings.”

Now that you asked them, it helps them realize that not only are you the right vendor, but that if they don’t do something, and do it now, their problem is going to get worse. 

---

Lesson? 

If you can move from just showing solutions to asking questions, you can help prospects go from answering just one question: 
- Why do something with this vendor? 

To answering all 3 Whys: 
- Why do anything?
- Why do it now?
- Why do something with this vendor? 

P.S. SE Leaders: For monthly tips on how to improve presales, join 200+ presales leaders who get our newsletter: https://lnkd.in/eKaaGeZr

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 the idea of "storytelling" in sales confuses you, watch this video.

I talk about the most important component of storytelling (creating contrast) by giving a simple real world analogy. 

Then I give an example of how you can apply this to B2B sales. 

I've had sales leaders use this exact video to teach their team the basics of storytelling.

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.

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.

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 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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I always hated the saying, "Time kills all deals." It's true. But it's selfish. Let's look at why, and what we should do about it.

In my consultative sales workshops, I always ask the team 3 questions: 
1- How long is your sales cycle?
2- How long is your implementation? 
3- How long before adoption/proficiency? 

Since most of my customers are selling big platforms, the answers are often: 
• 9+ months for the sale
• 3+ months for the implementation
• 6+ months for adoption

That's 18+ months before they get "value." 

Think about that for a second...

That means our customers are sitting in pain for 18+ months. 

So yes, "time kills all deals," but if we think about it from our customer's perspective, it's even worse! 

The longer we take to sell, the longer our customers are in pain!

This is why the absolute worst thing you can do as a consultative seller is react to your customer. Yet I see sales teams do it all the time: 
- Customer wants a POC, they get it
- Customer wants a demo, they get it

The real problem is that customers often don't know what they want, much less what they need. 

As a sales professional, you have to be able to constructively push back and lead your customer. 

They need your guidance and expertise. 

If you can't push back and lead them, you're not just hurting yourself, you're hurting them. 

You're the doctor. They're the patient. Never forget that.

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.

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," and not talking about 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 do this, you have the basics of a story. If you don't do 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?

Solutions Consultants when their Sales Rep starts talking about architecture...

Last week, I got to spend a day in DC with the Bloomberg SC team at their SKO. Here's why I loved it: 

1. Most SC training is focused on talking (demos). We did the opposite. We focused on discovery and dove into the Alpha Value Discovery Methodology. Because that's where deals are won and lost → discovery, not talking. 

2. We got to do this workshop style, not lecture style, so everyone was up and moving around, digging into business problems and uncovering value for their clients. Collaboration always wins.

3. This SC team has experienced pros, not rookies. The best thing you can do in that type of situation is create an environment where they can share their brilliance with their peers. We did exactly that. 

Thank you, Mackda, Jenna, Kara and Andy, for having me. Your team is absolutely amazing.

Senior Manager, Solutions Consultants - Tax at Bloomberg Industry Group

Senior Director of Sales Readiness and Enablement, Bloomberg Industry Group

Results-Driven Commercial Executive | Passionate about Building Teams | Running and Baking Enthusiast

B2B sales is the best job in the world. It's also the hardest. The most thankless. And the most strategic. But most people don't understand that. 

Most people think you just hire people who are convincing and like talking. 

But that's not at all what you do. 

In B2B sales, you have to hire people who are:
- good at listening
- good at asking questions
- good at getting people talking
- good at getting 15-25 people with different priorities to agree on something
- good at writing
- good at letting other people do the "selling" (SEs, CSMs)
- good at managing projects and stakeholders
- good at having business conversations
- good at asking people for money
- good at navigating relationships
- good at dealing with politics

...and good at taking it on the chin over and over and over again without taking it personally. 

To be successful in B2B sales, you don't need talkers - you need Leaders. 

This is exactly why I love it. 

P.S. What'd I miss?

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?

In the past month, 2 of my clients (1 VP of Sales, 1 CRO) have told me that their team is not selling at the CFO level. If you are trying to sell to CFOs and other C-Suite Leaders, here are 4 questions that you should be thinking about helping your client answer...

1. What’s the problem we’re trying to solve?

2. What’s the reason for the problem?

3. What’s it costing our organization? 

4. If we don't solve it now, so what? 

Until these 4 questions are answered, most executives don't even want to talk about solutions.

In other words, you could have the best product, but it doesn't matter because the problem isn't big enough to solve.

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!

Working with the next generation of professionals is both humbling and rewarding; I am constantly in awe at what these 18-22-year-olds are capable of.

I am no stranger to intern and collegiate programs; I worked as a Graduate Assistant for both of my master's degree programs, ran summer intern programs while at Showpad, and am back at it again with GTMshift and SolutionExec.

Thanks to an introduction from my friend George Kuruvilla, I am working with the CUBE program at the University of Illinois Urbana-Champaign. 

We have a team of business and technical consultants collaborating to develop a product that will serve as the foundation for how we build personalized experiences; for instance, the team is designing an adaptive platform that leverages user data to tailor content and recommendations to individual preferences.

After just a few meetings, I am super impressed by this team and even more thrilled to see the business folks leaning into the technical side.

This tells me that the future of business is more technical than it is today, as the next generation will have the savvy to work in ways we never knew how to.

We are excited to share more about our product over the coming months.

Thank you, CUBE!

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.

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.

Are you as tired as I am of the surface level event playbook where you walk away with no actionable takeaways? 

Good. 

Craig Rosenberg, Matt Amundson, and Jorge Soto are tired of it too.

So we are teaming up for "Engineering Tailwinds - The GTM Playbook for Winning in Hard Markets", an in-person one-day event with top operators who are building and living in this today. 

🗓 When: March 26th from 1-6p PT
📍 Where: San Francisco LinkedIn HQ 
👥 Who: Founders, CROs, CMOs, & Head of GTM for Series A-D companies

Oh, and more speakers to be announced soon too.

Apply to attend on Lu.ma: https://luma.com/w6x2lgd9

See you there 🔥 😎

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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