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

Vector

Vector, backed by YC, is building the future of B2B Signal-Based Marketing Intent.

Co-Founder & COO

Team Ignite Ventures

Venture Partner

Sales Engineers of Boston

Sales Engineers of Boston is a Greater Boston based networking community created to support and unite technical sales professionals. The SEBOS community harnesses the momentum of the ever growing Boston tech industry, standing as the premier platform for like-minded individuals to grow their professional network, source top local talent, and educate themselves on a wide range of careers in technology.

https://www.senation.org/boston

Founder

Drift

Director, Global Sales Engineering

Manager, Sales Engineering

• Responsible for hiring, retaining and developing the East Enterprise Sales Engineering team, the top performing region at Box.    
 
• Driving a technical sales strategy using solution-based approach, security evaluation and scoping implementation services with Box Consulting.

• Influencer to strategic customer information security teams around broader cloud security strategy, often providing insight into Box's integration with leading Mobility, DLP, eDiscovery, Identity Management and Encryption Key Management vendors

• Partner closely with the AVP & Sales Directors to strategize on accounts, brainstorm creative solutions and help architect a long-term vision for our customers. 

• Critical liaison between our customers, partners and Product teams - providing critical feedback and working on internal projects to deepen our competitive advantage.

• Present Box's GTM strategy around Platform, industry solutions and strategic partnerships with IBM/Microsoft

Manager, Enterprise Sales Engineering

• Top Performing technical sales leader dedicated to driving better outcomes inside large enterprise businesses, using a solutions oriented approach.  Focused on driving revenue and acting as a critical liaison to all customers' lines of business across multiple verticals.   

• Owner of the technical strategy as part of the customer account team, responsible for achieving the technical win & aiding in driving a deal to closure.

• Expert in leading complex demonstrations utilizing multiple softwares, API / Platform development and product integrations, that are customized for each client's need.

Sales Engineer, Enterprise

• Drive world-class Retention and Adoption in a portfolio of Box’s Strategic large enterprise customers.  A portfolio of over $10M in Box revenue.  

• Partner with customers in their digital transformation to become an expert in their business initiatives.  Educate clients on the benefits of Box, detailing our business model and articulating our value proposition.

• Alongside the customer, work strategically to develop a plan that maps customers’ objectives and results into an actionable success roadmap. 

• Partner with internal strategic programs teams such as Product Advisory Board and Executive Sponsor Program to cultivate and leverage strong stakeholder relationships at multiple levels of contacts.

• Maintain a deep understanding of the product and SaaS industry to guide customers through the most relevant features, functionality and software integrations.  

• Use analytical skills and leverage qualitative & quantitative tools to identify and map customer health metrics - such as product adoption and sophistication, relationship strength, customer satisfaction to better understand our clients’ changing business and technology issues.

• Function as the voice of the customer and provide internal feedback on how Box can better serve our business and these enterprise customers

Senior Customer Success Manager, Strategic Accounts

GE Aviation

• Responsible for the P&L of several GE Engine Services contracts, a portfolio worth over $600M.  Directed all activities providing the necessary support on pre- and post - contractual administration, management, Terms & Conditions of the contract.  Led customer engagement, relationship growth, commercial and technical contract actions.  

• Defined management  and execution of risk modeling activities in support of the future outlook of each contract.  Assisted in sales strategy campaigns of new contracts and program modifications.

Senior Customer Program Manager

JOLP is a two year, rotational program, spread throughout GE.  It is a unique experience to lead three different business positions which utilize military leadership skills, while developing new requirements to succeed in the corporate environment. 


GE90 / GE9X Business Operations
•	GE90 Lease Pool Strategy Manager
•	Interim GE90 / GE9X Marketing Manager
•	GE90 / GE9X spare engine sales support

Customer Support Manager  /  Customer Program Manager 
•	Customer-facing, GE representative for two of the fastest growing regional operators in the U.S.
•	Leads the development of customer relations and management of commercial support negotiations in a cross-functional team environment.

GE Junior Officer Leadership Program (JOLP)

United States Air Force

Directed, instructed and administered a professional education course to 350 annual Combat Systems Officer students in the Air Force Chief of Staff’s $400 million program.

• Advised unit leadership on daily decisions impacting 38 instructors, 350 students and 22 aircraft worth $118 million. Acted as front-line supervisor responsible for morale, discipline, safety and proficiency. Recognized by a senior ranking Commander as “Top 5% of 177 Captains.” 

• Designed and standardized continuity criteria for compliance inspection. Achieved an Excellent rating on team inspection with no discrepancies, utilizing a new streamlined training process. 

• Identified Commander’s Review processing deficiencies and improved efficiency procedures. Reduced unit-processing time by 40% using redeveloped guidelines. 

• Led and redesigned Emergency Management plan for 38 personnel and 22 T-6A aircraft. Appointed as sole operator by unit leadership to develop and implement contingency operations necessary for immediate action.

• Attended a 5-month T-6A Pilot Instructor Training course with an overall “Commendable” Instructor rating.

Instructor Pilot (T-6A), Senior Program Manager

Deployed as a representative in charge of strengthening the United States’ military and political relationships among several Middle Eastern countries during highly stressful, wartime situations.

• Established an airspace de-confliction plan in support of a joint and multinational large force exercise. Ensured coalition assets were prepared to execute immediate combat operations. 

• Co-authored and implemented a 24/7 operations plan to protect Jordanian border airspace during civil tensions in Syria, named as a foundation for future defense.

Program Manager, Foreign Air Defense Liaison

Commanded worldwide operations within one of the United States’ most technologically advanced aircraft.  Responsible for mission efficiency and the safety of aircrew members, cargo, and $202 million C-17A aircraft.  

• Ensured safe and efficient execution of 5,700 squadron flying hours, managed $4 billion in aircraft assets, all of which supported various United States Department of Defense agencies.

• Served as unit commander’s key asset and focal point for coordinating all staff functions.  Edited and processed all unit documentation on a daily basis for over 160 personnel.  

• Directed a financial project to improve unit defense travel budget discipline.  Reduced late reports by 55% and oversaw $1.2 million over 16 accounts with 100% accuracy.

• Commanded a 3-week mission to mobilize 25 armored vehicles to Afghanistan with a new route from an austere location.  Transported $12.5 million in assets, and saved $4 million annually using the new process. 

• Ranked by supervisor as “#2 of 28 peers in year group.”  Commended by Operations Commander as “#7 of 94 Lieutenants.”

Executive Officer, C-17A Pilot Aircraft Commander

Student pilot in rigorous Joint Specialized Undergraduate Pilot Training course.  Completed 89 hours of T-6A flight, over 100 primary flying hours in the T-1 aircraft and over 69 hours in T-6 and T-1 simulators.

• Maintained a near perfect 99% academic average in 23 exams covering over 388 hours of classroom instruction in the following courses: instrument and navigation procedures, weather, aircraft systems, aerodynamics, mishap prevention, cockpit resource management, and aerospace physiology.  

• Selected by instructor leadership as the Senior Ranking Officer for the second phase of Joint Specialized Undergraduate Pilot Training.  Led a team of 13 pilot training students to 100% pass rate over a 6-month intensive program. 

• Earned the Distinguished Graduate Award for finishing in the top 10%, the Leadership Award, and Air Education Training Command Commander’s Trophy for best overall program performance (#1 of 20).

Student Pilot

Hi, I'm Nick! 

I'm the Co-Founder & COO of Vector working to revolutionize how marketing leaders spend their ad budget in a far more effective fashion than in the past. 

I bring 10+ years of experience leading and scaling successful SaaS sales teams through best-in-class technology: 

- Director of Solutions Consulting at Drift (acquired by Vista)
- Enterprise Sales Engineer and SE Manager at Box
- Owning $35M/yr in P&L at GE Aviation
- United States Air Force Instructor Pilot and Program Manager

If you’ve read this far into my profile, let’s connect! 

Finally, follow me on LinkedIn for more insights on Contact-Based Marketing, the latest AI sales tools, and “how to’s” for running hyper-targeted marketing campaigns.

Nick Masters

A VC once told me, “You're too small to compete.”
I smiled and thought, we aren't picking you as an investor because you don't get it. He was running a playbook, the same one he's used over and over again, and refused to adapt.  

Small teams with a strong brand 👻 and grit are the ones that big brands fear the most.

That conversation happened 18 months ago. Today, Vector competes directly with companies 50x our size - and we're winning deals they can't touch. 

Shoutout to our content, brand, and creativity from Jess Cook, 👾 Alex Virden, and Sara McNamara. 

Small teams move faster.

Small teams stay focused. We don't have 47 product managers debating features. We build what customers actually need.

Small teams get personal. When a prospect emails at 9 PM, I respond. When our ICP is telling us about a trend that needs to be changed or added to the product, it happens in days, not months. 

The big platform companies are stuck in meetings while we're solving problems.

They don't know how to compete with a team like us that can make major changes overnight and deliver solutions they can't match.

✅ We close deals in weeks, not months
✅ We innovate without approval chains
✅ We customize without bureaucracy

That VC was right about one thing - we are small.

But small doesn't mean weak. Small means dangerous.

When you combine a lean team with relentless focus, you become the competitor everyone underestimates.

Co-Founder & COO @ Vector | Y Combinator | US Air Force

🤣 What if pop-up ads were happening IRL 🤣

In 1984, Jay Conrad Levinson came up with the idea of guerrilla marketing. He showed that the brands people remember are the ones that have fun. But losing is not fun. Losing stops creativity. When competitors are winning, all that’s left is feeling desperate.﻿

Here's how we operate at Vector 👻 when we get creative...

1. Emotion > Money

Most brands try to buy visibility.
We brainstorm ideas that make us laugh.
We understand impressions don’t equal attention.

2. Normal Is the Enemy

I’ve never seen a breakthrough come from a “safe” idea.
The ads that actually work? They’re the ones that don’t look like ads at all.
We tend to overemphasize our culture in our marketing.

3. Engagement Is the Strategy

Broadcasting to buyers is easy.
Inviting them into something worth paying attention to is hard.
We speak their language because we are just like them. 

Guerrilla tactics work for a reason:
Small teams with taste > Losing teams with lazy spend.

Creativity is still the biggest unfair advantage in B2B. 

When you let your culture leak into your marketing, you stop playing defense.
You stop chasing.
You start creating.

And that’s when your brand 👻 becomes the one people remember.

taplio

The Battle

Rew Dickinson

Nick Masters

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taplio

The Battle

Rew Dickinson

Nick Masters

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Rew Dickinson's LinkedIn Performance

Performance ScoreNick Masters's LinkedIn Performance

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