Sales Hiring Crystal Ball: How to Hire Sales Leaders Who Thrive

October 26, 2023

Editor’s Note: This is the second article in a two-part series on the future of SaaS sales. You can read part one here.

I recently caught up with an investor who was an operator during the recessions of 2001 and 2008. In the last year, he’s spent more time with founders and GTM teams in the SaaS startup space.

The common thread?

Many of these founders and executive teams are in their first or second startup over the last 10 years. They haven’t experienced a tough selling environment like the one we’re in now. And, put simply, it’s difficult to keep up when you haven’t experienced a difficult market.

Kevin Chiu, co-founder of Catalyst captured this idea in a recent LinkedIn post:

Kevin Chiu_LinkedIn

There is no magic bullet, pill or wand. It’s not just about one thing like product-led growth, inbound leads, renewals, product, marketing, net-new revenue, EBITDA, expansion, product, retention, or revenue that will help you in this challenging market… it’s about ALL of it.

Successful, sustainable businesses are ecosystems, not silos.

Startups that adopt a holistic, embedded business approach are the ones that will get through the hard that comes their way and emerge better for it. So how exactly might they do that?

Hiring for the Current Environment

One of the most common reasons early-stage founders work with me is to replace their executive Sales and Customer Success leaders.

Big outcomes and past success don’t necessarily translate into the skills or desire to keep up in today’s landscape.

It’s a multi-faceted problem stemming from:

  • Elevated titles without the competence to do the work required at that level
  • Over-segmented GTM functions
  • Prematurely quitting for a greener pasture when the hard times hit
  • First-time leaders who lack the right training, support, and infrastructure
  • High turnover among both hiring managers and would-be employees
  • Sacrificing potential and developing internal talent to chase the next milestone hire
  • Misalignment of expectations or assumptions

The points above have created a challenging skills gap that often results in a lower supply of leaders who can step up, endure and thrive.

Just a few years ago, the market was so frothy that many “A-Players” didn’t have to be that talented to produce great results, and employers had such a hard time hiring that important corners were cut.

It’s the same thing I hear when I speak to investors considering a new company… what was once considered an “A” investment opportunity is often a “C” today.

Suppose you were raised in sales as an inbound BDR focused on high-velocity SMB inside sales and were promoted to VP of Sales for inbound teams. It’s all you know so it’s naturally  your “playbook” for hiring, onboarding, coaching and forecasting.

What happens when you have to create an outbound strategy or shift into a different market segment?

We are in the middle of a correction period. We must think bigger to level up and support our teams to do the same.

B2B sales reskill

There’s no doubt we’re in a challenging environment. But it’s also important to note that nothing changes unless we change it. It’s hard to fix what you don’t understand. And getting to the root is the first step.

Merely swapping people in and out or blanket training doesn’t fix what ails you.

It’s like a house, you can’t build infrastructure if the foundation is cracked. So look for an experienced hire – someone who’s been through the good and bad, not someone who just happened to be in the right place at the right time.

Clarity Is King

Before making any hire, let alone one in sales leadership, it’s critical to get clear on these details first:

  • Why this hire/why now
  • The work that’s required to do the job well
  • How you’ll define success and the milestones to get there
  • Lessons you’ve learned from previous hires
  • Your role in helping them succeed

And then create and use a hiring scorecard backed by an effective hiring process.

Fooling yourself into thinking you’ll know what good looks like when you see it, relying on your gut, or using the process to figure out what good looks like on the fly increases your chances of costly mishiring.

Sales interview red flags

Pro Tip: Ditch the idea that it’s OK to burn through sales leaders until you find the right one. Going in with the mindset that the first few won’t stick sets everyone and everything back.

Get Uncomfortable

Bill Gross, founder of Idealab, has been involved in 300 rounds of financing and 35 successful exits since 1996. He points out that founders often hire people similar to themselves because it’s more comfortable and easier to build rapport quickly. But Boston Consulting Group found that companies with diverse management teams realized a 19% increase in revenue compared to their less diverse counterparts.

In reality, growth is hard and uncomfortable. Look for people “who are most unlike you and most complementary.”

For the first time in my life, we have five generations working together in the workforce. And they all bring something unique to the table. But when I think about the conversations I have every day in the startup ecosystem, ageism is alive and well.

Take an honest look around your executive table and business…The last recession was in 2008. If you, your team, or your investors haven’t seen a downturn or a recession and are struggling, it’s time to choose differently. Choose someone who has a Ph.D. in course correction. They’ve seen a thing or two, learned from those experiences, and can use that perspective and knowledge to help you.

Being an effective “wartime” leader is hard if you haven’t seen the fight before or expect others to fight it for you.

Hard Thing About Hard Things

Ditch bias and know exactly what you’re going for, find it, and make it happen.

And, as with any hire, validate their skill, will, and the “lean-in” factor to set you up for success. Hiring the right, experienced executive who has already accomplished a similar goal is a blessing, not a curse. 

Alignment Is the Name of the Game

ATP alignment

Hiring excellent people creates excellence. But it’s pointless if you can’t keep them.

Ben Horowitz talks about this in his book The Hard Thing About Hard Things too:

“My old boss Jim Barksdale was fond of saying, ‘We take care of the people, the products, and the profits – in that order.’ It’s a simple saying, but it’s deep.”

It’s easy to say you want to create a great place to work. It’s hard to fulfill that promise in practice. There are a few keys ways to achieve alignment:

  • Ditch the idea of selling someone and get to the practical details in the hiring process. When you’re aligned, you don’t have to sell.
  • People don’t expect perfection, they want honesty. Don’t make promises you can’t keep about growth or compensation. It’s okay if you don’t know, talk about how you might get there together.
  • Communicate expectations early and often, even when it’s hard or the last thing you want to do.
  • Ditch assumptions, seek to understand and validate instead.

Choosing Differently for Long-term Success

I’m grateful for two lessons I learned early in my career during my first recession in 2001:

  1. Understanding and being accountable for every part of the customer journey. Doing so made me recession-proof and a better seller, leader, advocate for my customers, and entrepreneur. Merely focusing on one part of the funnel holds a business, customer, and sales career back. How can you close a conversation if you can’t open one and vice versa?
  2. The power of having a business discussion. I grew up selling services before products. There was nothing to demo. Instead of feature dumping, hoping something would stick, I had to understand how to have highly visualized conversations while considering the short-term and long-term.

Feature dumping on your leads and hoping something sticks isn’t a sustainable GTM strategy.  Knowing the difference between features and an embedded platform is key:


These are easy to swap and replicate. They’re a smaller piece of the puzzle. Focusing on features promotes “talking at” our customers while merely skimming the surface, leaving many opportunities untapped.


An embedded approach where technology, services, features, and products come together to help a customer on a deeper level. This kind of solution promotes “talking with” the customer to confirm alignment, even when the deal is done and it’s time to expand or renew.

Delivering a highly valued product depends on understanding that features are small bits of functionality that accomplish smaller tasks, and products are a collection of many factors, including features, while addressing key concerns like governance, compliance, and security.

Understanding why customers engage and make purchasing decisions is the golden ticket. Think about your business today. Can you clearly articulate the seven reasons why your customers engage and how you can help them:

  1. Solve a problem
  2. Reach a goal
  3. Get better
  4. Pinpoint blindspots they haven’t yet considered
  5. Be the hero of their story, not yours
  6. Reduce/remove risk
  7. Create a new or easier way to make money

Supporting your team to do this work consistently will help you avoid an outcome like this:

Angie Judge_LinkedIn

Wrapping Up

Steve Jobs said it best when Apple was dangling by a thread, “I think the way out is not to slash and burn, but to innovate – that’s how Apple got to its glory and I think that’s how Apple could return to it.” Innovation is the key to success in times of crisis. The only way to innovate is to spend time with your team and customers, look for the themes and blindspots, and take action to address it.

The world is changing fast. Outdated, one-size-fits-all growth formulas are a thing of the past. Remember, frameworks are flexible, and playbooks are rigid. Hiring leaders who have been there and seen it before to navigate uncharted waters is one of the keys to your success.

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.