The 4 Enterprise Sales Misconceptions for Startup Founders

September 10, 2020

Closing a blockbuster multi-million dollar deal with a Fortune 100 company can be a massive win for a startup.

But don’t get too attached to the idea without knowing what you’re getting into.

Enterprise sales is not a simple switch to make from SMB sales—it’s a completely different beast.


I recently caught up with a founder I talked to last year who didn’t have the time (or desire) to deal with sales and wanted to hire someone to ‘”validate the market” for him. While his product was interesting, I respectfully declined as I could see the danger ahead.

Fast forward to more than a year later and he resurfaced. According to him, the salesperson/leader he hired wasn’t able to validate the market, their product wasn’t going over well with their customers, their churn was high, and it was the mis-hire’s fault.

As I dug deeper, it was clear a lot of the wrong assumptions had been made without an understanding of what enterprise sales is all about.

If he replaces the hire but still has no idea what the market needs, how is that going to stop the bleeding? After all, the marketplace speaks the loudest, and without customers you don’t have a business.

Enterprise sales requires an entirely different level of experience and skillset to be successful. As a startup, you can’t afford to dive into the deep end without knowing how to swim.

It’s a challenging market segment to tackle as you can’t take a one-size-fits-all approach. But if you do your research, prepare and develop a bulletproof (and repeatable) sales process you can set yourself up for long-term success. The key things here are patience, prioritization and quality engagement to create lasting results that truly scale a business for the long haul.

Make no mistake, it’s not something you just decide to do and the success immediately follows.

These are the four misconceptions founders struggle with the most when it comes to “going up market.” Understanding them is essential to avoid making costly mistakes that could jeopardize the future of your startup.

Misconception #1: Enterprise sales is easy

Let me be clear. Even if enterprise leads are falling in your lap, there is nothing easy about enterprise sales if you want to stick around for the long haul.

And if you’re used to dealing with SMBs, get ready for a big change in your process.

SMB sales cycles have faster timelines and fewer buyers in the journey, and they don’t require integrations or customizations, aren’t as strategic, and are far less complicated.

Compare that with a process that takes at least 6+ months to complete and has a ton of complex, moving parts along the way:

Source: Gartner

Talk about a buyer journey!

This is why you need experienced salespeople on your team who know how to navigate the enterprise market. Otherwise you’re destined to lose a lot of money and time along the way while burning bridges with mega buyers.

But if I could boil it all down, enterprise sales is about helping through a consultative lens versus selling.

“Good salespeople sell lots of product, but great salespeople make lots of customers successful.”Mark Birch

Think project management, research, planning and consistent communication (internally and externally) with a multitude of influencers and decision makers.

But wait… there’s more!

Product-market fit is key. If you truly can’t help your buyers solve a problem, achieve a goal or fundamentally get better, the world of churn awaits even if you squeeze a deal through.

With a process that’s strategic, complicated and long, there’s little room for mishaps along the way.

Misconception #2: Don’t hang onto your buyers

Many of the startups I talk to are hyper-focused on one thing: getting new customers and adding more shiny logos to their website.

It seems like founders these days are convinced that their only way to succeed is to put all of their efforts into growth.

Churning and burning your customers is NOT the way to achieve sustainable growth.

In fact, it’s a good indicator you’re en route to losing a lot of money over the long-term. Why do you think so many companies are talking about retention these days? The effects of customer churn compound over time.

The chart below illustrates how costly customer churn can be over the long-run:

Think about it: If you net just 0.25% more revenue each month, you’d earn $21M more than a company running at a 5% monthly churn rate.

When you’re talking about enterprise sales, “churn and burn” is a recipe for disaster.


As a startup—and especially in the enterprise market—you should be laser-focused on getting new customers and providing each of them with exceptional service that makes them want to stay with you for a long time.

This means addressing the evolving needs of your buyers to create win-win solutions that move the needle for their businesses.

Here are three ways to put your buyer first while emphasizing customer experience to bring in new logos while hanging onto them for the long haul:

  1. Understand your clients’ evolving needs
  2. Relate to clients on their terms
  3. Communicate early and often to set mutual expectations = win/win

That’s where the real magic of growth happens.

Misconception #3: “I’ll just promote my inside sales rep to enterprise sales as my first enterprise salesperson.”

Oof. This can be a recipe for disaster.

Not to sound like a broken record, but… enterprise sales is a whole different ball game.

One of the main reasons companies reach out to us here at Avenue Talent Partners is because the wrong person was brought in for the job.

I recently spoke with a founder who had an SDR, inside sales team and the funding to build out an enterprise sales function. But here’s where they went wrong: They promoted their top inside sales person to spearhead their move into the enterprise market.

See, this person had never been in enterprise sales before and was thrown into the deep end. They struggled to map out the right territory plan, didn’t know how to map out their buyer journey, couldn’t nail the discovery process, and ultimately failed to connect the dots for their buyers. They were treating prospects as highly transactional deals to just shove through their repeatable SMB sales process and it showed in their results.

They were rapidly approaching the 12-month mark and nothing had been sold with a lackluster pipeline that would tell a different story in the future.

If you jump into enterprise sales without the appropriate experience and knowledge of the current market, it’s not going to end well— especially as a startup.

Please know that you truly only get one shot at the enterprise sales table, so don’t risk diving in before you’re ready. Especially if you don’t have the right person in place to help you build that part of your business.

Patience is a virtue, but consistency is also essential here. You need people on your team who are experts at building and nurturing relationships for the long haul, not convincing them to get a deal done hoping it will stick later.

Remember: You’re not just selling your product to a company, you’re selling to influential people within that company.

This is where the long-game mindset serves you well, and I can’t stress enough how important it is to build a world-class enterprise sales team that has the know-how to navigate, implement and succeed in this market.

With the right foundation in place, you can start winning and nurturing your customers so they stick around for the duration.

Then—and only then—you’ll be able to reap the rewards.

Misconception #4: “Let’s just show them the product and they will lose their mind.”

If only it were this easy.

It’s rare (think unicorns, not snow leopards) that your product is going to be a slam dunk for any enterprise buyer. I have yet to see a product that met the needs of an enterprise client perfectly without customization or a complex integration process.

Approach each buyer with a desire to understand what they’re facing from all angles. It’ll take a lot of work to get all of the key decision makers (multi-threading in enterprise is 7+ people and growing) on board.

Remember: You’re not selling buyers a product. You’re selling a solution to a problem.

Neil Patel really hit the mark when he talked about the importance of being a consultant and resource, rather than a salesperson.

You want to be the person on your buyer’s speed dial whenever an issue arises.

And the only way to get there is by accumulating deep market expertise, which is not something you can just fake to get a deal done.

If you’re getting into the enterprise market, you need to commit to it fully. That means having an enterprise team that can fully immerse into your buyers’ worlds, know exactly what their struggles are, and show them that you have the skills, knowledge and expertise to identify and solve their problems for a long time.

Even if a buyer likes your product at the outset, don’t get caught in the illusion that the hard work is done.

At that point you’re just getting started.

Wrapping up

Enterprise sales is a different kind of animal. As much as I love it and have had success in this segment, it’s not the holy grail that every startup should aspire to.

If the SMB and mid-market segments are lighting your world on fire, it’s absolutely okay to swim in the lane that serves you the best.

That said, if you know your product can serve customers in the enterprise market and you’re ready to commit to building out an effective enterprise sales function, it can be your ticket to more lucrative deals, expanded networking opportunities and solid long-term clients.

“Stop selling. Start helping” –Zig Ziglar

It’s important to understand that successful enterprise sellers are viewed as trusted colleagues first and foremost. They never forget how important it is to be students of their buyers in order to understand how they can help best!

Choose wisely.

Header photo by #WOCinTechChat

Founder and CEO of Avenue Talent Partners

With more than $100MM in revenue sold, a LinkedIn Insider and Top Sales Voice, Founder, Strategic Advisor, and LP at Stage 2 Capital, Amy Volas is a sales fanatic turned entrepreneur. She was bitten by the startup bug many moons ago and couldn't imagine spending her time anywhere else. She created Avenue Talent Partners to help grow early-stage startups through some of their most valuable assets - executive revenue leaders.