Learn Like Mongo, Join Like Stripe

A tech GTM career goes through ebbs and flows. Sometimes, you are selling a product that sells itself; other times, you are grinding to close the smallest deals.

However, both types of experiences are important to appreciate the two components to loving your day-to-day:

1. Being the best at what you do

2. Joining a company where their product is so good that anyone could sell it

Chris Orlob, an early hire at Gong, had a post that summed up this point with a good story:

His next lines were:

He's spot on here, but unless you get lucky to start your career, you must earn the right to get the job at the "easy to sell" company. Hundreds of people are interviewing for a fraction of those roles, most seeming good on paper or an initial call.

The two organizations that exemplify these two concepts are MongoDB and Stripe.

When I think through some of the best deal-process and qualification experts I've met or listened to on podcasts, it's the MongoDB sellers who were there pre-IPO.

MEDDPICC. Command of the message. Relentless with their time. And yes, some of these folks come off as sales-y, but I've been impressed with a decent amount of folks I've met from there, both in sales and business acumen.

When I think through the best opportunities to be a seller? I think of joining Stripe in the mid-2010s. Insane product-market fit. Inbound demand. Cerebral sellers. Technical product. Client love. Rebranding of GTM.

These folks had it good, and as Meka says in this clip, "We had too much inbound, we didn't know what to do with it." Or as an old VP of sales there told me, "It was an inbound qualification game more than anything."

How else could you recruit people from Bain to get into tech sales? Give them an opportunity they can’t refuse, aka Stripe in 2015.

A dream situation to be in as a seller.

I'll break down both:

Become so good at selling that you could sell a weak product if you had to.

Constantly building your skills and having a growth mindset is something I see the top sellers do.

This is pretty obvious, but here are several tips I've seen been helpful on how to skill build:

• If you’re selling enterprise deals, use MEDDPICC for your qualification framework

• If you’re at a company that gives Command of the Message training, consider yourself lucky and lean into that

• Make it a habit to constantly review your Gong calls / put them into Claude to see how you can improve - I like reviewing 1-2 discovery calls a week and 1 non-discovery call (like a pricing call) and thinking of one thing I could have done better

• Consistently ask for feedback from your manager and ensure you are taking only 1-2 things each week to work on. Incorporate that into your calls that week and review them again the following week to shorten feedback loops

• If you aren't getting the coaching you need from your manager (sometimes this can be a co-founder or a general head of GTM who has never sold before), ask them to hire a sales trainer - two awesome ones that come to mind are Peter Ahn or Dakota Mckenzie

• Check out Pclub.io for some of their classes

  • Note: Some of these tactics they give are a little sales-y, but for the most part, you can repackage some of it into what makes sense for your sales

  • I've liked these classes in particular:

    • Selling With Champions & Discovery Masterclass

• Listen to other top performers on your team - I have learned a ton from Taylor

• Read books/listen to podcasts to supplement what you're learning on the job, really love SPIN selling and some of Jeb Blount’s books

• Ask for feedback from your SAs

  • Sometimes, getting feedback from your peers is hard because they feel awkward. I always like to say, "Hey, I'd love feedback, and it helps me know my blind spots. I promise you won't hurt my feelings - I want to get better. Anything that comes to mind on what I could have improved on / what I could do more like top reps you've worked with?"

• Improve overall business acumen - no, you don't need to spend money on an MBA (although some of the best sellers I’ve met have strong academic backgrounds), but books like Personal MBA and reading the WSJ daily can help close the gap if general business terms are foreign to you

Join a company that builds such an amazing product that you could sell it even if you weren't very good.

I wrote about this in an earlier GTMBA article: It's the biggest paradox in sales: The best reps sell the easiest products.

What makes a good sales environment/job? Here are the 11 that I initially wrote about:

1. High Talent Density: Smart colleagues who elevate you and your future career

2. Inbound Lead Flow: More leads than salespeople; qualify instead of hunt

3. High-Growth Company: Series A-D company growing 100% YoY with proven PMF

4. Path to Enterprise: Can sell big deals for high compensation

5. Hot Industry: Sell products in fields you're genuinely passionate about

6. Technical Products: Sell to engineers; build valuable, respected technical expertise

7. Beyond Just Selling: Contribute to marketing, strategy, and product development

8. Modern Leadership: Data-driven leaders who avoid outdated sales tactics

9. NYC/SF Presence: Located where top GTM talent congregates

10. Fast Shipping: Technical founders who iterate quickly on product

11. PLG Model: Allows prospects to try before they buy

However, they've earned that right join these orgs because they relentlessly focused on GTM skill development or business acumen (or, in rare cases, just got lucky)

Google in the 2000s, Stripe in the 2010s, and now OpenAI/Anthropic in the 2020s.

Some might say these folks had/have it easy, but hey, good for them - they're doing something right.

All it takes is one "yes" to getting into these orgs, and then you're in the talent orbit. It compounds, making it easier to get future jobs because the easiest way to get a job is to have internal references pulling for you: "I've worked with X, and they're amazing. I can speak to them." That's how you get hired about 80% of the time.

If you aren't there yet, keep grinding. It will get easier once you have a talent density and network tailwind.

If you’re grinding through a tough opp right now, remember that it’s prepping you and forcing grit/skill development that will pay off and help you become a better seller. This flywheel stands true:

Skill development is at the core of limiting future hardships - it’s important to be so good they can’t ignore you.

Control what you can. Combine best practices from those who joined the Mongos and Stripes of the world in the 2010s.

Be so good they can’t ignore you (controllable), and join an organization so strong that anyone can sell their product (eventually, controllable as well).