What’s Next for Sales? 6 Steps to a Sustainable Sales Practice.

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

Every week I have conversations with investors that usually go something like this:

Me: “What are you seeing in your portfolio.”

Them: “The rocky ride isn’t over yet.”

Me: “Tell me more.”

Pattern and theme recognition is one of my superpowers, and I can’t help but notice that conversations like this are common – and persistently so. In this article, I’ll share more about what I’m hearing from investors, sales leaders, and customers, why the ride is still “rocky,” and what you can do to help.

The Current Selling Environment

Now more than ever, the race is on for startups, many of which are facing:

• Dwindling runways
• Leaky pipelines
• Costly churn
• Disjointed executive teams
• “Vitamin” not “painkiller” status
• Misalignment between price and value
• Attempting to go up-market to bridge a big gap
• Too many pivots that aren’t given enough time to settle in

The reality is sales isn’t one-size-fits-all. And the way that many grew up in it, built their careers, and found success over the last 10 to 15 years isn’t going to cut it now.

The popular formula for growth is proving to work less and less.

In short, it’s a heck of a lot harder to raise money, buyers are demanding more, the market is consolidating cluttered verticals, a correction is happening, and what got you here isn’t going to get you through or there.

Regardless of market segment, most deals are taking longer, more people are involved in a deal (the bigger/more complex the deal, the more people and different departments are involved), spending is scrutinized more closely, and, put simply, it’s just harder to sell. This is especially true in the enterprise segment, where so many startups are chasing big dollars:

It’s hard to watch so many well-intended startups try to solve their GTM challenges with ineffective long-term strategies like:

• Throwing bodies at goals or problems.
• Building and scaling a sales team prematurely – you can’t scale what you haven’t validated.
• Pushing net-new logo acquisition with little consideration for expansion or retention. According to Gartner, 60% of technology buyers involved in renewal decisions regret nearly every purchase.
• Oversegmenting the sales function. It alienates the customer and decreases sales productivity and quota achievement. LinkedIn’s 2022 State of Sales research shows that the highest performing cohort “always” put the buyer first, with 70% exceeding quota by 50%.
• Dragging sellers down with too many tools, administrative tasks, and internal meetings. Plus, insufficient training and coaching, bad compensation plans, and KPIs that incentivize the wrong behaviors and outcomes for your sellers and business.
• Making sales a “sacrificial lamb” for the business because it’s easy to measure. Remember, a business is the sum of its parts, not just the one that looks the best on the outside.

6 Steps to Build a Sustainable Sales Practice (Even Now)

In sales, it takes the right people in the right roles to do the right work using the right process to grow a sustainable business. Here’s how to get there:

1. Understand your business is unique.

Instead of trying to keep up with everyone else, mute the noise and get honest about your metrics, demands, limitations, and goals.

2. Ditch assumptions.

It’s hard to grow or recover if you don’t know what good looks like – good people (employees and customers), good processes/systems (leadership), and good delivery (across the company, not just sales). Auditing and analyzing strengths, weaknesses, opportunities, and threats in these key areas is a productive starting point to confirm or deny your perception while also rooting you in reality. It’s also a valuable way to illuminate new challenges or opportunities hidden below the surface.

3. Clearly articulate answers to questions like:

• Do you know your niche? The riches are in the niches. Trying to be everything to everyone is only costing you time and money.
• Have you validated your ICP? A handful of small deals in big logos is not enterprise validation.
• Have you crossed the chasm? Early adopters do not equate to market validation. Moving from early adoption to the early majority is a critical part of growth and risk. You can’t grow if you don’t learn from your initial customers while validating and confirming ICP. This focus sets the foundation for future growth. Risk comes from a lack of focus – trying to be all things to all people in an overblown TAM.
• Do you have the infrastructure to deliver, expand, customize, integrate, and retain?
• What are the patterns between your pipeline, forecast, timing, and sales process stages?

4. Embrace OKRs (Objectives and Key Results).

While KPIs (Key Performance Indicators) are good data points for measuring progress, they don’t provide critical context or guide the team’s overall direction.

5. Ditch the rigid playbooks and lean into frameworks.

Frameworks are adaptable, flexible, and require ongoing strategic thinking. Being able to adapt on the fly is key in a fast-changing market.

6. Explore the full-cycle sales model.

What’s old and proven is new and effective for your business, the customer, and the sales profession. Without a solid pipeline, there are no buyers. Without buyers, there are no customers. And without customers, there is no business.

So far, in 2023, 82% of businesses that failed did so because of cash flow problems (Fundera). It’s hard to fix a cash flow problem if you’re attempting to fix it the same way as everyone else who’s struggling.

Startups that emphasize excellence with people, customers, data, and systems to inform their strategy are more effective. The read, rinse, repeated, one-sized playbook is not.

“People always ask me, ‘What’s the secret to being a successful CEO?’ Sadly, there is no secret, but if there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves.”

– Ben Horowitz, The Hard Thing About Hard Things

Making Sense of the Shifting Sales Landscape

Revenue starts and stops with the customer and their outcomes. Yet we tend to make it all about our goals and outcomes, alienating the people who write our checks in the process.

How many times have you heard about a deal tanking because the key decision maker left, or that the pressure is on to cut costs from their Finance team, or maybe that the seller has decided to go back to square one?

It’s not just about “multi-threaded, “discovery,” or the 10-point sales checklist between the Ops, Marketing, Sales, and CS teams that’s going to get the deal done. Selling today needs to be about a cohesive and strategic approach that reaches beyond KPIs and demos.

So how does this shake out in practice?

• Customer focus: It’s about their outcomes, not products or features. To do this well, meet your prospects and customers where they want to be, not where you insist they be.
• Organization: Blueprint the customer to understand their org structure, the teams involved, what they care about, what’s happening in their industry, and knowing what a good customer looks like for your business.
• Discovery: It’s not a one-and-done “step” in a sales process. Instead, think of every interaction as an opportunity to understand.
• Mutual Action Plans: Work with the customer to pinpoint expectations, deliverables, timetables, and assigned steps… together. This gives you a proactive way to confirm alignment every step of the way.
• Ability to have a business conversation: A point of view resulting in knowing how a business works (P&L, OKRs, annual reports), preparation, and research to confirm/deny what makes sense together.
• Multi-threading: Manage the posse of decision-makers, stakeholders, and key influencers (ignoring power users or key influencers that validate executive decisions is a deadly sales sin)
• Compensation: Audit the behaviors and outcomes you’re incentivizing

All of this sounds fine enough, but how do you actually support your team to make this happen?

Training

Each person on the team is unique and learns/retains information differently. Try to meet them where they are to provide onboarding, coaching, training, mentorship, cross-functional opportunities to learn about the business and bite-sized masterclasses. This applies to executives too.

Full-cycle Sales

There’s a gap between expectations and reality when you’re building your business around a ‘growth at all costs’ mindset. You think you’re building an efficient and seamless sales process, but you’re actually doing the opposite leaving your buyers with a lackluster experience.

Instead, think about how you like to purchase things – do you like to be handed off? A buyer wants to know how you can help them while feeling heard, valued, and understood. Not getting funneled through a forced process. It’s efficient and productive to have one person working to achieve that outcome together with the customer.

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There’s no question that selling today is harder than ever. But understanding the landscape, why the market is the way it is, and what buyers want to get out of their experience with both you and your product will help close the deal.

All of that’s great, but if you can’t find, train, and retain the best people for your business to do it, you won’t get very far. This is why in the next part of this series, I share tactically how to find and hire the right sales talent given today’s selling environment.

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