The future of sales, according to a Harvard professor

Published: Wed, 10/15/25

Updated: Sat, 10/18/25

October 15, 2025

TOGETHER WITH

Welcome back to The Quota. We hope you’re having a great, closed-won day. In this week’s highly-caffeinated issue, we’ll interview a Harvard Business School professor about the current state of sales. After that, we’ll share a Sales Fail about lunch, and give some advice to a rep being asked to work before getting hired. Enjoy the show!

NUMBER OF THE WEEK

Opportunities closed within 50 days have a 47% win rate, compared to 20% or lower after that threshold.

Source: Outreach

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

Amazon Web Services wants its AI applications to gain more traction organically, without leaning heavily on sales teams. Rivals have seen better grassroots adoption than AWS's coding assistant, while larger enterprise customers tend to favor Microsoft's GitHub Copilot, according to an internal Amazon document obtained by Business Insider. The push to ensure organic traction points to changing dynamics in the software sales ecosystem. You can read more about it here.
A Mercedes saleswoman went viral after posting a message for young buyers: Don’t buy cars you can’t actually afford. Stacey Allen says dealership protocol prevents her from telling customers not to sign papers, even when she knows the deal isn’t in their budget. She says too many young buyers get dazzled by a Mercedes that looks like a steal—because it’s much cheaper now than when it rolled off the lot —without realizing what they’re signing up for. You can read more about it here.

FEATURE

The Future of Sales with Harvard Business School Professor Frank Cespedes

A lot has changed in the world of sales since our 2022 interview with Harvard Business School professor and author Frank Cespedes. We sat down with him again to get his view on the current state of sales and how he sees it changing in the future. Below is an abridged version of the interview. You can read the full interview here.

1. In our 2022 interview, you mentioned that sales was becoming more data-driven and technology-dependent. Three years later, what's the most significant change you've observed in how B2B sales actually gets done?

Over the past three years, among the biggest factors impacting sales and business development are the end of more than a decade of very low (in real terms, negative) interest rates, and the uncertainties spawned by up-and-down tariffs and other factors.

Higher interest rates mean higher cost of capital and the end of growth-at-any-cost, which characterized business development in many industries. It means a return (a welcome return, in my opinion) to profitable-growth sales requirements. Meanwhile, both higher interest rates and uncertainties have lengthened selling cycles in many B2B categories.

Those factors require firms to get better at lead generation and lead qualification. Longer selling cycles increase the costs of chasing false positives—prospects that you spend a lot of time on but that don’t buy. You need to identify a false positive sooner rather than later, because of the reality of opportunity costs in every business. Money, time, and people spent chasing account A are resources not available for accounts B, C, D and so on.

In most companies, these implications pose significant change challenges. Sales metrics usually focus on top-line volume, irrespective of profitability or cost-to-serve different types of customers. So, from the sales force’s perspective, there are no ‘bad’ customers. In many comp plans, sales reps have no incentive to identify a false positive and move on. Doing better, more actionable account reviews becomes a more important sales management activity. Territory assignments and sales deployment often need an overhaul.

The reality is that if you’re a sales manager, your job has gotten more complex and demanding in the past few years. But whenever I hear managers complain about this, I always quote that line in the gangster movies: “Remember, you chose this life!”

2. Every sales tool now claims to have AI features. From your perspective, where is AI actually making a measurable difference in sales outcomes, and where is it just marketing hype?

You are right to use the word ‘hype.’ With AI, we are in the early stages of a familiar tech hype cycle. One reason is that AI is now a loose term for many different things, some of which are driven by evolving large-language models and many of which are just using “AI” as a slogan.

That said, the value proposition at the heart of AI is that the tools can do some tasks nearly as good or better than people, freeing-up time for people to do the tasks they do best. In sales, freeing-up time is a big deal.

For example, most salespeople spend less than 50% of their time in actual customer contact. Estimates are 30-35% and this figure includes emails, phone calls, webinars as well as virtual or in-person meetings and demo’s. Consider the impact in a business of increasing time spent prospecting or selling/servicing customers by an incremental 10 – 20%. In most companies, that’s a major productivity boost and it increases the addressable market, because economically infeasible segments become feasible with better go-to-market utilization.

However, I’m old enough to remember business “reengineering” initiatives in the 1990s. The slogan then was “don’t just use technology to pave the cow paths.” That remains true with AI. If your sales model is not relevant or reaching diminishing returns because buying patterns have changed, no amount of AI will help.

Focus first on the sales process, and then AI tools. Without up-to-date understanding of how target customers make decisions today (not yesterday), you won’t know where AI capabilities can make a difference. And that understanding is a management, not a technology issue. Without it, AI easily becomes a tool without a real use-case or just another cost of doing business.

3. Cold email deliverability has tanked, LinkedIn is saturated, and buyers are harder to reach than ever. Which channels or approaches are you seeing work for prospecting in 2025?

“What goes around comes around,” and that’s always true with marketing media. A decade ago, many organizations cut resources for email campaigns in favor of SEO and other search media. Then, as the pandemic made online search a very crowded and expensive medium, they flooded customers with emails again.

That cycle should be expected and anticipated. Current best practices will always be imitated and, as that practice saturates a given medium, the ROI of that approach inevitably declines. That’s called competition. Good managers know how to track diminishing returns and move on to an approach that generates better ROI for some time.

For example, my experience with companies is that email, when targeted at the right prospects at the right time in the buying cycle, is still a relatively effective medium. But as technology makes email blasts such an easy thing to do, many sales people use it indiscriminately and, in effect, train their customers to treat their emails as spam.

In addition, as I’ve argued in my own research and books (and in our 2022 interview), sales is a context-specific business activity. Selling software differs from selling capital goods which differs from selling professional services. Selling in the U.S. differs from selling in Asia which differs from selling in Latin America or the Middle East. And even within the same geography and category, customers differ not only in their preferences for products and services—the basis for market segmentation—but also in how they want to interact via email or webinar or in-person, and so on. The job of the sales person is to understand those differences in their customer base and then use, or not use, the relevant tool, whether it’s email, LinkedIn, the phone or whatever.

By contrast, searching for some secret-sauce, all-purpose tool or approach is, in my view, a sucker’s game. What’s the managerial implication? Go back to basics: do we know who our target customer is and is not? Have we developed an Ideal Customer Profile (ICP) that helps sales people prioritize prospecting criteria, call patterns, and communications media?

I suggested a process for developing an ICP in a book I wrote a decade ago, Aligning Strategy and Sales. I think that advice remains as relevant as ever. In fact, the process itself typically has value: it helps to establish a common language and shared vision across product, marketing, and sales functions which generates benefits in areas beyond email or LinkedIn expenditures.

Read the full interview here.

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Warning: This book will not make you successful. But it might keep you sane.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

When was the multi-level knife sales company Cutco founded?

A. 1977
B. 1896
C. 1964
D. 1949

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I had an intro call scheduled with a new prospect at 1 PM. I'd been in back-to-back meetings all morning and was starving, so I ordered Uber Eats timed to arrive at 12:30. Plenty of time to eat before the call. Except it didn't show up until 12:58.

I grabbed the bag, set my burrito bowl just off-camera, and joined the video call with my stomach growling. The guy had his camera turned off so I decided to turn mine off as well. 10 minutes in, I realized this guy had zero budget and no decision-making authority.

The guy was rambling about his business, so I muted myself to take a huge bite. Then he asked me a direct question. I frantically tried to chew and swallow, unmuted, and attempted to answer with a half-full mouth. I said. "Sorry, had something in my throat." This happened four more times throughout the call.

Every time I tried to wrap up, he'd launch into another story about his previous vendors or ask about stuff we don't even offer. I'm pretty sure he noticed because he asked if I had another meeting coming up. I lied and said yes, hoping he'd wrap it up. Instead, he started talking faster, trying to cram in more questions.

The call finally ended after 45 minutes. The guy thanked me for my time and said he'd "think about it" (which means never). My burrito bowl was room temperature and soggy. I scarfed down the rest of the bowl in 10 minutes before I had to hop on another call. I've never been so frustrated eating lunch in my life.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- October 2025

WORTH A PEEK

This economy is weird. So is anyone actually selling anything right now? This question was recently posted to Reddit, and the answers give us a glimpse into which industries are thriving, and which ones are… not. Check out the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I’ve been interviewing for an AE role at a fast-growing SaaS startup. The process was going smoothly until the VP of Sales said they “like to test candidates in the wild” and asked if I’d come in for a day to make real outbound calls using their CRM.

It’s not a paid trial, just a “chance to show how I sell.” They even mentioned I could use their leads and “maybe book a few demos.” I want to prove myself, but it feels like they’re trying to get free labor out of me before offering the job. Is this normal, or a red flag?

Skeptical in Location Withheld

Dear Skeptical,

Trust your gut. This isn’t a “test,” it’s unpaid work. A real evaluation might involve a mock pitch, role-play, or case study, not calling actual prospects for free. If they value you, they’ll want to see how you think, not how many demos you can book before lunch. Tell them: “I’m happy to do a role-play or presentation, but I’m not comfortable reaching out to real clients before joining.” If they insist, walk. Good luck!

Quiz Answer: D. Multi-level knife sales company Cutco was founded in 1949 (You can read the source article here).

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