Leading a sales team is one of the most challenging jobs you can have.

Don’t let anyone tell you otherwise.

You’re partnering with cross-functional leadership. Inspiring frustrated reps. Establishing effective processes. Hiring A-players. Building compensation plans that lead to retention. Navigating tools. Holding compelling sales team meetings. The list of responsibilities goes on and on. All in the name of one ultimate goal.

Hitting quota.

The Top 25 Sales Management Articles of the Last Decade

At Ambition, we’ve spent years understanding, studying, and enabling effective sales leadership. We’ve read and published thousands of articles, but there are a handful that have truly defined, shaped, and codified modern-day sales over the last decade. 

Get your bookmarks ready. In chronological order, this is our list.

1. An Argument for Specialized Sales Teams. David Skok interviews Aaron Ross. 2012.

Aaron Ross and Marylou Tyler set the world on fire when they published Predictable Revenue in the early 2010s. This article marks a turning point in the history of sales: the moment when sales leaders began adopting more segmentation, new playbooks, and new hybrid outbound methodologies that would define sales for the next decade.

2. The Healthiest Sales Team Culture I’ve Ever Seen. Mike Weinberg. 2013.

Mike Weinberg’s Sales Management, Simplified is another must-read sales book from the last decade. The 8 qualities of a healthy sales culture he shares (taken from a real-life sales organization he witnessed) are as integral now as they were in 2013. A timeless read for sales leaders.

3. If SaaS Products Sell Themselves, Why Do We Need Sales? Mark Cranney. 2014.

A pivotal read for anyone working in SaaS sales leadership, with plenty of crucial, applicable takeaways for sales leaders operating outside of the SaaS universe. Every sales leader knows it’s important to have a sales team that can answer these 3 critical questions at the drop of a hat: Why change? Why now? Why you? 

4. People Don’t Buy What You Do. They Buy Why You Do It. ROI Group. 2014.

Another seminal work that transcends sales, Simon Sinek’s TedTalk, book, and the thousands of corresponding blog posts they inspired warrant a mention on this list. Applicable from a sales leadership and a direct selling standpoint.

5. 10 Secrets to a Successful Sales Meeting. Mark Hunter. 2014.

This simple list from legendary sales consultant Mark Hunter is a thing of beauty that spells out the core tenets of a successful internal sales meeting. No steak knives required.

6. The Right Way to Use Compensation. Mark Roberge. 2015.

Roberge became a legendary folk hero in the sales world for his work at Hubspot and subsequent contributions to the worlds of sales and marketing as an educator and researcher. Compensation is crucial to incentivizing behavior and retaining your sales force, and Roberge lays out the foundation for a successful compensation plan beautifully.

7. How to Scale ARR to $50M. Jacco van der Kooij. 2015.

Jacco van der Kooij inspired more successful SaaS organizations than almost anyone in the last decade. You’ll hear Catalyst CRO Mark Kosoglow (formerly VP of Sales at Outreach) credit him for giving him the playbook that scaled Outreach in a later article, and this treatise is a must-read as well for anyone leading a SaaS sales team.

8. The 7 Attributes of the Most Effective Sales Leaders. Steve W. Martin. 2015.

An excellent summary of exhaustive research conducted by Martin for Harvard Business Review, this quick read manages to both convey the ROI for an effective sales leader and the core attributes that make them great. A must-read. 

9. To Clean Up Your Startup’s B.S., Bring Sales Into The Leadership Team. Lars Dalgaard. 2015.

There was a period in the mid-2010s when Silicon Valley tried to convince people that truly high-powered startups didn’t need a sales team. This phenomenon led to sales leaders and their teams being treated as second-class citizens in many nascent companies. This article from Lars Dalgaard led the backlash and has been proven correct time and time again. In this day and age, it’s hard to believe this topic was even up for discussion. 

10. The Sales Director Who Turned Work Into a Fantasy Sport. Ethan Bernstein and Hayley Blunden. 2015.

A fun read about outside-the-box sales leadership inside Fortune 1000 Clayton Homes. Great sales leaders are always looking for innovative ways to inspire their sales teams and gain an edge, and this article highlights one of the best examples we have seen.

11. The Sales Influencer Series Presents: Mark Kosoglow. Mark Kosoglow. 2016.

Our interview with former Outreach VP of Sales Mark Kosoglow tells the story of Outreach’s massive growth from Mark’s vantage point. We learn everything he did as an original VP of Sales to build his team, set goals, create a sales stack, and establish processes that led to Outreach’s unicorn status.

12. Only 1 in 7 Sellers Do This Crucial Skill. Jill Konrath. 2017.

One of the most beloved and important sales gurus of the 2010s, Jill Konrath is a household name in the modern sales organization for good reason. We love this article from Jill as a use case for sales leaders to implement into their organization and a characteristic to look for when hiring and evaluating sales reps.

13. 12 Sales KPIs that Made Me a Better Sales Manager. Max Altschuler. 2017.

Sales Hacker Founder and Former CEO Max Altschuler was kind enough to outline the top 12 sales KPIs that helped him lead his sales team. A great set of examples for you to steal.

14. Effective Sales Leadership Boils Down to These 2 Words. Steve Richard. 2018.

Steve Richard has brought so much value to the world of sales over the last decade, his inclusion on this list was a no-brainer. In this article, he boils effective sales leadership down to its most atomic level, preaching consistency and accountability as the name of the game. 

15. Create a High-Performance Sales Culture with These 7 Habits. 2019.

There’s an old saying that culture can either be formed intentionally or organically. As a sales leader, your mission is to intentionally build a sales culture that facilitates the revenue results your team needs. In this blog post, I outline exactly how to do it.

16. Account-Based Sales Lessons Learned: 2016-Today. Trish Bertuzzi. 2019.

The Queen of All Things Sales over the last decade, Trish Bertuzzi has been the authority on all things account-based sales and sales development. Her comprehensive coverage of the two subjects in this article is equally applicable today as it was in 2019. Give it a read.

17. Goal Setting. John Barrows. 2019.

Heralded sales consultant John Barrows delivers a short, sweet, and powerful message about goal setting in this blog post. A great read for sales leaders looking to establish goals beyond mere quota for their teams (and those who mistakenly believe they don’t need ‘em).

18. The Ultimate Guide to Sales Coaching. Chris Orlob. 2019.

Gong has hosted one of the best data-packed sales blogs on the planet over the last decade, and this authoritative text from its purveyor Chris Orlob might be the highlight. An invigorating read that is still relevant in 2023. 

19. Sales Culture Eats Strategy for Breakfast. John Waid. 2019.

A wonderful write up that frames sales leadership in a way we’ve never seen before. Waid establishes priorities for every sales leader to follow when leading their team. You’d be wise to read and pay heed.

20. As Your Sales Team Scales, Focus on Your Middle. Tomasz Tunguz. 2019.

Moving the middle percentage of your sales team performers is something we’re fond of promoting here at Ambition. The laserlike insights of the inimitable Tomasz Tunguz on this topic are a must read. 

21. What Sales Leaders Need to Excel Over Time. Andris Zoltners, Prabhakant Sinha, and Sally Lorimer. 2019.

The very suggestion of term limits for sales leaders is misguided, in our opinion, but the rest of this article from the HBR authors is not. There are some great highlights the authors make about hidden traps sales leaders can fall into that sabotage their performance over time. A great read for any sales leader that will bring some self-awareness about potential pitfalls lurking around the corner. 

22. How to Sell. Gary Vaynerchuk. 2019.

The polarizing yet influential Gary Vaynerchuk had an active 2010s. While his main focus was marketing, he has devoted a great deal of time to the subject of sales. His deep dive article How to Sell is so elemental that everyone must admit GaryVee knows what he’s talking about when it comes to sales. A useful way for sales leaders to get a fresh look at the subject.

23. On Sales Coaching and Driving Results. ExecVision interviews Keenan. 2020.

We couldn’t leave our man Keenan off this list. This quick hit excerpt of a talk he gave for ExecVision highlights some of the most obvious ways sales leaders are falling short when it comes to sales coaching. 

24. 10+ of the Most Common Mistakes in Early SaaS Sales. Jason Lemkin. 2021.

This article shares 24 articles about what to do and 1 article about what not to do. You can count on the legendary Jason Lemkin to add a valuable, unique perspective when it comes to sales. His writeup of the most common mistakes in early SaaS sales had great takeaways for anyone in a young (or dysfunctional) B2B sales organization.

25. How to Manage 100+ SDRs Across 4 Continents. An interview with Lars Nilsson. 2022. 

The Godfather of Account-Based Sales. It’s only fitting we end this article with Lars Nilsson, whose methodology was practically non-existent a decade ago and now seems to be everywhere. This is a great thousand-foot view on how Lars leads a massive sales force at what may be the world’s most successful tech company. Take a look.

The Top 25 Sales Management Articles

What are the top sales management articles that made you a better sales leader? 

We hope you give the articles on this list a read and learn from some of the most renowned sales leaders and experts out there. Get more tactical resources here to help you take your sales coaching and leadership to the next level. 

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