New and exciting tools, ways of thinking, and ideas draw our attention. Some foundational elements that worked well 10+ years ago still work well today, but others do not, and it's imperative modern sellers and sales leaders understand the difference.
The second half of my 30+ year career in the consulting field has been spent in sales, sales leadership, and senior executive roles. Throughout my journey from bag-carrying seller to CEO, I’ve always stayed close to sales processes and cycles.
Here’s what I think has evolved - and what’s remained the same.
Jump to a section: How sales has evolved | Three shifts | How sales hasn't | A recommendation
How Sales has changed
Today’s B2B buyers are far more sophisticated than at any time in the past.
The days when companies would buy software and services with linear buying processes —whether to automate new processes or keep up with the latest trends—are long behind us. Back then, the rush to spend on technology sometimes felt like the "irrational exuberance" former Fed Chairman Alan Greenspan described during the dot-com boom.
Today, nearly every organization is tech-savvy, and most have a solid understanding of how to purchase enterprise solutions and the services that support them.
Now, companies are much more cautious and strategic in their buying decisions. Spending is scrutinized more carefully, and the decision-making process is slower - with more people involved in the purchase decision, such as Finance and IT.
The days of quick, unchecked purchases are largely behind us. These are just some of the ways selling has evolved, but they can be summed in simple phrase:
Lack of Influence.
Sales has far less influence than ever before. As Gartner has shown, buyers are much later in their decisions before we as sellers get in front of them:
“Research reveals that 75% of B2B buyers prefer a rep-free sales experience.”
If they’ve requested a demo or a quote, chances are they’ve done the same with 2-3 of your competitors … and that’s after having whittled down an initial list. They’ve avoided you as long as possible and are ready to make a move.
So, what are some ways this balance has functionally shifted … and what it means for you today?
Shift no. 1: Access, Differentiation, and Trust
Years ago, sellers had a ton of influence over buying cycles because of the ability to build relationships. You’d be able to read a room and develop a good rapport with clients and prospects.
Building trust is a lot harder to do when you're meeting with people on Zoom, Teams, etc. because the body language isn’t quite as evident, there is no small talk before and after the meeting – and most frustratingly of all, you have no idea what they’re Slacking each other about while are presenting to them.
You lose the opportunity to create influence and build that relationship and that rapport. Champion enablement has become so much more powerful than before because those are the people going to bat for you in conversations you’ll never know took place.
This also makes it far more challenging to upsell, as a well-informed buyer has already talked themselves out of many of your available options before you’ve discussed them.
Further, the technology and services markets have exploded, and there are orders of magnitude more options from among which buyers can choose, and therefore must evaluate as part of their due diligence.
For this reason, buyers have so many meetings, and investing time in building relationships with sellers is often seen as a time-waster. They want you to get to the point of the meeting/presentation, then get out!
And so, the personal touch often gets lost.
When you're selling into this environment, you have to provide moments of value to the customer in every conversation, so they'll be willing to take extra time with you.
What does this mean?
You must be exceptionally well-versed in your customer’s company, industry, moment-in-time influences, and the business outcomes they are trying to achieve so that the ideas and solutions you bring to the table will actually help them – at every turn and meeting during the sales process – whether they eventually buy from you or not.
After all, a buying decision is, at its core, a matter of trust in you and your representations about what you’re selling.
Shift no. 2: Buyers have already done their research
A decade or more ago, the sales rep was the primary source of information Buyers consumed about the products and services being sold.
Now, by the time you first become aware of a “lead”, there is an excellent chance the buyer has already traversed ⅔ or more of the buying journey, through their own self-guided discovery & research efforts, and there are few remaining days and opportunities to influence the buying decision.
Take a recent buying process I went through - buying a used car for my son.
15 years ago, I’d have needed to step onto the lot, test drive, get information on available packages, pricing, etc.
I already had all of that information from my own research, YouTube reviews, and manufacturer & dealer websites. I knew exactly what I wanted to get, with which option packages, and what a fair price would be, so I just walked into the dealer and said “I'm looking for this vehicle with these certain packages” and bam, there you go.
There was no opportunity for the seller to influence me per se, and I feel like that's part of the dynamic here with B2B selling, as well.
Shift no. 3: Sales Technology
There is so much more available today. Too much, in many cases.
As Harvard Business Review published, “sellers who feel overwhelmed by technology are 43% less likely to meet quota than non-overwhelmed sellers.”
From intelligence tools to intent data, lead list building to automated cadences, the list is enormous. These tools can help you create significant market awareness through marketing, and (attempt to) identify companies and prospects showing buying intent behavior.
How technology is used matters greatly.
For example, you may have a tool like ZoomInfo, Apollo, Clearbit, Seamless, etc. These are used for database enrichment, outreach sequences, and pulling in lists of relevant targets to prospect (to name just a few use cases).
There is no excuse to show up to a meeting unprepared without a solid understanding of the company, their recent history, financial statements, and more. If a prospect is active on LinkedIn, that’s even better for your preparedness and ability to engage. Today’s modern sales tools can accelerate and improve the quality these preparatory and research tasks, that used to take hours and days to perform.
These capabilities are essential, with today’s buyers engaging later in their buying journey than ever before.
For the sales manager, these “self-guided” buying journeys and closely-guarded procurement processes also make forecasting more difficult, because you have less data from real-world engagement with prospective buyers upon which to evaluate your pipeline.
By the time you, as a seller, have first contact with a lead, you have to recognize you are already behind the game – you need to catch up, fast, and even with some help from intelligence tools and engagement platforms, the pressure is on to be as effective as possible in a limited number of interactions.
How Sales is still the same
I think the most important thing in selling is alignment to a customer’s goals and objectives - and have a process that allows your discussions and follow-up activities to support that.
This hasn’t fundamentally changed, even if it’s a key separation between great sellers and everyone else.
For example, companies (especially with higher-ticket purchases, such as enterprise software or services that go with it) always have an ROI-based business case to justify the investment they're making. It will be scrutinized by key stakeholders or the full buying committee and we won’t be in the room when they’ve having these conversations.
And so part of our job as sellers is to understand not just what that business case is, but why they are building the business case. In other words, what are the business outcomes they're trying to achieve by implementing that software or engaging the services that support the company's strategy overall.
If we can understand those things, we can understand how to relate our value proposition better to align with what the client is actually trying to achieve. And that's a multi-step process.
Some items include:
Buying Committees. Even if who’s part of the buying committee has shifted (Finance and IT are much more involved), understanding the key stakeholders and catering to each of them remains essential
Decision Criteria. What yes/no questions need a “yes” for a deal to progress?
Criteria Mapping. How do these decision criteria map to each person on the buying committee?
Value Proposition. How does the customer’s objectives impact how we provide value?
Champion Enablement. When conversations occur without our knowledge, have we equipped our biggest fan within the company to go to bat on our behalf?
Ensuring consistent execution of close plans is also a challenge for sales leaders, because the path to signature is where things can easily fall apart.
The Battle For Time
Sellers have always battled against processes that take away from their ability to sell. Salesforce’s own research shows reps spend 30% or less selling.
I’ve already mentioned ways that 30% can be challenged and has evolved, but ensuring sellers can sell is a struggle any sales leader likely resonates with.
Some of this is to be expected. After all, I want my reps:
Building account plans and knowing their customers
Keeping their deals updated and realistic - pipeline hygiene is important for forecasting
Reviewing closed-lost deals to understand what we need to do differently
Engaging and building rapport, such as on LinkedIn posts (and adding value, not just saying “Great post!”)
Aligning with Customer Support on potential cross-sell opportunities based on available information and interactions
What I don’t want them spending time on?
Labor-intensive administrative tasks that could be automated
Guess-and-check list building activities
Wading through systems to generate a quote
Fixing quotes due to errors
Chasing invoices
This is where I have to act like a seller and promote our Salesforce services (sorry…), including around AI and Agentforce, but no matter what platforms you use, understanding the how is important.
At the end of each year quarter, I like to talk with reps and get their feedback on what platforms they like vs. what they don’t. It may identify additional training that’s needed to better-adopt a tool … or show me something we don’t need to pay for.
One recommendation
I want to talk specifically to sales leaders for a moment, and then to sales reps.
Leaders, if you’re struggling to identify the strategic areas of investment (likely due to a shortage of time, not desire), it’s time to pull in a third-party and initiate the necessary discussions around processes, tools, influences, and more.
A roadmapping exercise not only drives this forward, but also enables more cross-team selling exercises as you should have other key teams involved in the discussions.
It's a client favorite for good reason!
Reps, if you’re struggling, I’d advise two points of consideration:
How are you spending your meetings with prospects and customers? Are you selling, or are you actively engaging and looking to build relationships and add value? (Your audience knows the difference)
What technology helps you be better, and what seems to just get in the way? This feedback is vital for your leader to make more informed decisions.
Sales is a challenging, but rewarding field.
It’s why I’ve spent my the latter half of my career in it, even as CEO here at DoubleTrack. We’re the ones on the front lines of revenue attainment for the company and who understand what prospects and customers want best.
And that likely will never change.