Nick Masters

Former US Air Force pilot. Building Y Combinator alum. I write about B2B sales, GTM, founder life, & leadership.

[Nick Masters @NickMasters83]

The best feedback I ever got was that I needed to give better feedback. Here's how I approach it now:

Three parts, in order:
Situation. Behavior. Impact.

𝐒𝐢𝐭𝐮𝐚𝐭𝐢𝐨𝐧: Over the last few months.

𝐁𝐞𝐡𝐚𝐯𝐢𝐨𝐫: You haven't been showing urgency to learn about the industry we're working to change. I've noticed this in basic questions you've asked—questions you could have answered by researching the field, checking Slack for documented answers, or testing the use case yourself.

𝐈𝐦𝐩𝐚𝐜𝐭: When someone stops to answer these questions, it distracts them from their own goals. And when you outsource your curiosity, it takes you further away from becoming the confident, consultative expert that customers trust.

It doesn't attack anyone's character or assign labels. It explains what happened, what I observed, and why it matters. It's specific enough to act on, but neutral enough to be heard.

Don't end with "go learn more." That's just a demand with no direction. 

Instead, ask: What's stopping you from becoming a true expert in our product, success stories, competitors, and the use cases that win deals?

This shifts the focus to a conversation about obstacles rather than a lecture about effort. You might uncover that they're overwhelmed with meetings. Or they don't know where to find the best resources. Or maybe no one has ever explained the expectations clearly.

Feedback is never meant to be a personal attack. The ONLY purpose is to give someone a path to make them better.

[Nick Masters @NickMasters83]

@danmartell smart people use social media to learn. dumb people use social media gain followers.

[Nick Masters @NickMasters83]

@davegerhardt A podcast opportunity should be 100% personal brand focused.

[Nick Masters @NickMasters83]

@asmartbear hire people who don't care about title at this stage. They need to care far more about building a successful business than their personal career optics.

[Nick Masters @NickMasters83]

@NickB2005 also learn to talk to customers without slides. too many people use these as a crutch to talk about the thing they should be experts in. The moment a slide deck comes up is the moment the audiences is being talked at and kills conversation.

[Nick Masters @NickMasters83]

@wilczyn more important than ever to build in public. don't have to share all your secrets, but you need a brand and personal expertise that builds trust faster than your competition.

[Nick Masters @NickMasters83]

It took me years to understand that the candidates who challenged me in interviews were usually the ones I respected most. We are hiring AEs at Vector and set a high bar for who we think will be the most successful.

When I joined the US Air Force, I assumed military culture was just people following orders without thinking. This was the case in the early days when you know nothing, but as you gain experience, which you gain fast, your job is to question (respectfully) the orders to make sure the outcome is correct and the risk is tolerable. This shows dedication to the mission and being part of the solution. If something did not make sense, asking about it was part of doing the job well.

I eventually realized that same instinct shows up in great interviews.

Hiring managers are looking to hire for experience because they have a problem that needs to be solved, and candidates who nod along to everything and overly complement the strategy are just trying not to rock the boat, get to the offer stage, and not lose the opportunity.

This might feel polite, but it tells me very little about how much real thought this candidate put into the role. A candidate who isn't chasing an offer shows confidence that they know they are going to get hired for a great-fit role, and not just ready to take anything.

Next time you are in an interview, show up with confidence. Make sure the hiring manager has FOMO about you as a candidate...

- Ask hard questions about competitors

- Push back thoughtfully on the direction of the product

- No company is hiring because everything is perfect; force the HM to clearly outline all the challenges that need to be solved with this position. Ask why these problems got to this point and weren't solved earlier.

The best hires I have made were not the people who tried to win me over by saying yes to everything.

Those who showed up confident enough to force me to question our own direction proved to me they might have better ideas and experience than I did...and they stood out across the rest of the candidates.

An interview is not supposed to be a test of loyalty. Do everything in your power to truly envision yourself in that role and make sure it's the right fit.

[Nick Masters @NickMasters83]

@sri9s Hard to reach these levels no matter what, but being too stealth hurts the ability to develop a strong brand. Don't be late building your personal and company brand because this takes so much time to build trust.

[Nick Masters @NickMasters83]

@Chris_Orlob It's also the #1 metric for defining PMF. People love to experiment, but you can't sell a lofty vision to someone who already has the product. You MUST sell the value they have experienced.

[Nick Masters @NickMasters83]

@araseb_ Founders typically lean toward being very technical without GTM experience. Building a strong product that would "sell itself" used to be the way, but today, marketing and strong sales methods are more important than ever to stand out among the noise.

[Nick Masters @NickMasters83]

@paulg Isn't this similar to when sales changed to Account Executive?

[Nick Masters @NickMasters83]

@bradmenezes Been following your path the last two years...making major directional changes is so hard for a full company to get behind, but when it works it's incredibly rewarding. Congrats.

[Nick Masters @NickMasters83]

@morganjingram but the human creates relationships that are authentic and caring. That's where sales reps/leaders win...when they actually care about someone else and not hitting quota.

[Nick Masters @NickMasters83]

@Codie_Sanchez I define my freedom as doing what i want, when i want, with who i want, for however long i want. Sometimes this takes money. But sometimes it's just discipline.

[Nick Masters @NickMasters83]

@BillAckman Anytime your company becomes a verb, it's usually a sign of future success.

[Nick Masters @NickMasters83]

https://t.co/dcRp7P48oU

[Nick Masters @NickMasters83]

[NEW] Things are changing in the AdTech space...quickly.

OpenAI is testing an ad format in ChatGPT where the click does not take you to a website.

It opens a business-specific agent! ChatGPT crawls your site and auto-builds a profile of your business, common customer questions, support info, general context. You configure an agent on top of that with custom instructions, product feeds, MCP connections for live business data, and your own lead capture forms. Campaigns run against the agent. It is in Ads Manager now for a limited set of advertisers.

Digital advertising has run on the same architecture since the first banner. Buy attention, send the click somewhere you control, let the page do the convincing. The landing page of a company's website has been the most focused marketing asset for decades.

This removes the page.

This strategy moves from copy to context. What your agent knows about your pricing logic, your objections, your inventory, is what performs. Companies with clean product data and sharp positioning will look like better advertisers than companies with better designers.

Marketers...what do you think about this approach? Does this take your expertise and creative skill away?

[Nick Masters @NickMasters83]

@alxberman Word of mouth marketing is the most amazing network effect…and it can’t be manufactured by the company. It’s all about having a great, valuable product.

[Nick Masters @NickMasters83]

@NickB2005 And they don’t try to chase the algorithm or gamify ways to get impressions. Their approach is simple…share useful content the audience cares about.

[Nick Masters @NickMasters83]

“How do you go from military pilot to tech sales?” I was asked this by a sales candidate in an interview yesterday.

It was genuine curiosity (a great sales trait)…and someone who was trying to connect the similarities of seemingly unrelated roles.

They are far more similar than you think:

Pilots have…

* A team to support them
* A mission with a clear goal
* A deadline that’s either pass or fail

Sales reps have…

* A team to support them
* A target account list to drive them
* A quota that’s either pass or fail

No matter how disconnected you think your past is, you have learned skills to make your current role successful.

[Nick Masters @NickMasters83]

@hannah24_app Never build features. Build solutions. Build outcomes. Now more than ever, this is what people need