If you’re in the U.S., I hope you had a great Thanksgiving (and maybe even snagged a deal or two on Black Friday). As we settle into the weekend and gear up for the week ahead, I wanted to shine the spotlight on a great deal of our own.
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Now, let’s jump in…
I speak with 3–5 SaaS executives every week — typically S/VPs of Customer Success, Chief Customer Officers, and Chief Revenue Officers.
Over the past 18 months I’ve noticed an uptick in CSM teams reporting directly to Sales or a CRO.
Some might be alarmed by this trend, but I’m not.
Aligning with Sales offers customer success leaders a chance to build new skills, elevate their careers, and demonstrate their value in driving revenue.
In fact, I often argue that many CS leaders already have what it takes to lead commercial teams.
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Many CSM teams already use account management playbooks. They act as the main point of contact for an assigned book of business, run regular business reviews, identify expansion opportunities, and often facilitate renewal negotiations.
But many shy away from being too “commercial.” They fear discussing contracts and pricing will erode their trusted advisor status.
I reject this notion.
If we can't trust the people who negotiate pricing, then no customer would ever sign a contract — the ultimate demonstration of trust.
The best salespeople earn trust while selling — and it’s more critical now than ever. With competing products looking more alike, free trials becoming standard, and prospects completing 70% of their research before contacting Sales, trust and helpfulness often tip the scales.
If this sounds familiar to you, it should. Many customer success managers already excel in this high-trust, consultative context.
If you squint, it's difficult to see the difference between one software vendor and another in the same category. Convincing someone to buy from you versus a competitor requires rapport and trust. The best customer success teams know how to build relationships grounded in value.
The best customer success managers also listen more than they talk. They look for the customer’s pain and position solutions accordingly. They have a genuine interest in helping the customer improve.
“Anytime you’re tempted to upsell someone else, stop what you’re doing and upserve instead. Don’t try to increase what they can do for you. Elevate what you can do for them.”
Daniel Pink - To Sell Is Human
Great CSMs act like consultants, offering benchmarks, insights, and challenges to customers’ thinking. They also provide recommendations and share common practices based on their experience with other customers.
CS leaders often come from operational backgrounds. A well-architected sales process — clear stages, milestones, and deal status criteria — is where they shine, leading to higher conversion rates and more predictable sales results.
To excel as revenue leaders, CS pros need to build and hone a few additional skills. Adding these skills increases the likelihood of success in a revenue-generating context and can help propel one's career toward senior management.
Negotiation
Great sales leaders excel at negotiating. They understand how deal levers (e.g. price point, scope, payment terms, contract length, etc) work together. And they work to create win/win situations by balancing what the customer values and what their company values in a commercial relationship.
Managing by numbers
At some level, sales is a numbers game. Want to drive more pipeline, closed-won deals, and revenue? Prospect every single day, follow up on every lead, push each active sales opportunity forward every week.
Coaching & accountability
Not only do great sales leaders drive activity volume, they assess and enforce quality. They join sales calls and provide regular coaching and feedback to frontline sellers. Call recording tools now make it easier than ever to review and coach on the frontlines.
Strategic planning
Sales leaders create plans to tackle their market, segment, or territory to ensure they hit their number. They have a clear sense of who their prospects are, how to engage them, and how they will go about developing and closing opportunities with them.
Influence & persuasion
A prospect’s preference for the status quo will often torpedo a sale before a competitor does. To combat this, you have to know how to educate and persuade buyers to act.
This may be the most uncomfortable part for customer success folks. But think of it this way: If you believe in the product you sell, and you can map it to the customer’s pains or needs, then your goal is to help by persuading them to adopt it.
Financial acumen
Great sales leaders understand the fundamental language of business. They help customers understand ROI in both a financial and non-financial sense. They also know how business and legal levers affect all parties. (I'd argue this is a skill every customer success leader should possess, too.)
Sales requires urgency, hustle, resilience, and adaptability — traits that can’t be taught. One either possesses them or they don’t, and there’s very little gray area in between.
The transition from Customer Success to Sales isn’t about abandoning your roots — it’s about recognizing sales as the first step in improving customer outcomes.
By embracing this mindset, customers success professionals can unlock growth — both for their customers and for themselves.
Are you one of the many customer success teams that now sit in the sales organization? How have things changed? Or stayed the same?
Hit “Reply” and share your thoughts.
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