Sales leaders and CEOs: Here’s how the best sales reps evaluate your AE opportunity

Since 2015, RevsUp recruiters have had the privilege of working with some of the very best software salespeople in the industry. We’ve learned a lot about what motivates these top performers and what they’re looking for in a new opportunity. Based on the thousands of candidate conversations we held last year – and the hundreds of job offers accepted – we've identified 10 factors that consistently rank at the top of their list when evaluating a potential sales position.

The purpose of this article is to share some of this aggregated data with hiring managers. We seek to answer two questions. First, when true Top 10 Percent sales reps are evaluating new opportunities, what are their most important criteria? And, as a CEO or VP of Sales, what can you do to improve your standing in these areas??

For any firm, landing the very best salespeople can mean the difference between gaining a 5% market share in 2023 or 25%. Earning a Series B round of funding or burning through your remaining cash. Posting about your successful exit on LinkedIn or posting your resume. So, are you aware of how these closers are evaluating you, and are you doing everything in your power to make your opportunity more desirable to them?

Top talent consistently rates the 10 factors below as the most critical when considering a move; crucially, they are listed in order of relative importance.

1. A history of financial success among the current salespeople on the team.

Money talks, and top-performing salespeople want to work for a company where they can make a lot of it. Financial success is one of the most critical factors that salespeople consider when evaluating a new AE opportunity. They want to see that the current sales team is achieving their sales goals and that they are being rewarded appropriately for their efforts. If your current sales team is making a lot of money, it sends a clear message to potential new hires that they too can achieve financial success with your company. Typical salesperson questions: What percentage of the sales team beat their quota last year? What did the No. 1 rep earn? How many people made it into accelerator territory?

2. A potential new boss who can articulate their vision for the sales team and has a rich history of producing quota overachievers?

Sales reps want to work for a supervisor who can inspire them, motivate them, and partner with them to achieve their professional goals. So, the best sales reps look for a boss with a documented history of growing headcount and revenue year after year, and with some exits under their belt. You understandably communicate to recruiters, “I really want to hire salespeople who have long tenures.” My friends, this goes both ways! One sales VP told me during our discovery call, “I’ve produced $1 million earners at four consecutive companies, and I have no plans to let that streak be snapped here.” You can imagine the interest this leader generated among top performers! Typical salesperson question: Why does this sales leader only stay 18 to 24 months at each job?

3. A well-designed lead-generation and demand-generation operation.

The best sales reps are happy to hunt for new opportunities, but they also want to be supported by a thoughtfully created lead-generation and demand-generation engine. They want to work for a company that has a top-shelf tech stack (CRM, contact databases, email automation, LinkedIn automation, etc.), as well as at least a minimal amount of SDR support. They want to know that the company has a clear plan for generating leads and that it will provide the resources they need to succeed. Typical salesperson question: Among their closed deals, what percentage of the leads are AE-generated (self-generated), and what percentage is generated by all other sources combined?

4. A large and viable Total Addressable Market – both now and over the next 3 years.

RevsUp typically works with companies with between 100 and 1,000 employees, and one of the main draws of that profile is greenfield territories. Nothing frustrates top reps more than being confined to seven ZIP codes as a patch or a worn-out named account list. Is the company planning to flood the market with salespeople over the next 12 months, or are they committed to making the existing team successful before scaling again? Top AEs also want to know who they’ll be selling against; for example, other early-stage startups or industry giants like Salesforce, Oracle, Workday, etc. Typical salesperson question: Roughly how many targets are in this company’s Ideal Client Profile, and what percentage of them are already using something like (COMPANY)’s solution?

5. Clear, consistent communication regarding your workplace policy: work-from-home, work-from-the-office, or hybrid.

Our research is clear when it comes to workplace preferences. 40% of our candidates will not consider working even one day a week from an office; 20% are actively seeking a role that features a strong office culture with consistent attendance; and 40% will consider coming into the office a few days a week if required. Because the vast majority of employees have strong feelings about this topic, it’s fairly easy for a hiring manager to navigate. If your company has non-negotiable requirements regarding office attendance, you just need to clearly communicate them. Just understand that each new non-negotiable will reduce the number of viable candidates to which you have access. Typical salesperson question: Is there any flexibility with their work-from-office policy?

6. Publicly available content that validates your customers’ satisfaction with your solution.

Sales reps want to work for a company that has happy customers. They want to see logos, case studies, video testimonials, and ratings and reviews on third-party product-review sites like G2, Capterra, and SoftwareAdvice. They want to see evidence that the product is meeting the needs of its users, and that it has a track record of success in the market. Not only do these materials give an AE confidence, but they’re used by AEs every day for prospecting activities and discovery calls. Every rep loves to see a robust website and social media presence. Typical salesperson question: What percentage of their active customers renewed last year?

7. A fair, well-communicated experience during the interview process

Candidates believe that a hiring manager’s approach to the interview process is predictive of that person’s leadership style. What do we look for in great leaders? Candor. Transparency. Clear expectations. Crisp communication. Urgency. Empathy. Organizational skills. Fairness. The ability to influence internal stakeholders. Core values on display. Does your hiring process reflect these attributes? Sales reps want to know how many interviews they can expect, how long the process will take, and what they will be evaluated on at each stage. This information helps them plan their time and resources effectively, and it demonstrates that the company values their time and effort. Typical salesperson question: How long did it take the last person you placed here to get hired?

8. Glassdoor ratings and reviews.

While there is always a debate about the veracity of Glassdoor reviews, over the years I’ve found these ratings come pretty close to matching what the actual employees tell us during our interactions with them. If you’ve created an above-average sales culture, your effort will be reflected in the reviews and help you hire more top talent. I advise CEOs that have a weak rating (say, below 3.5) to directly ask their employees (across all divisions of course) to contribute to Glassdoor. Do not in any way try to influence the results. Try messaging the company some version of this: “Please be fair, but honest. We will read the reviews carefully and take action where there are opportunities for improvement.” Typical salesperson observation: This is the first time I’ve seen a company culture described as ‘venomous’?

9. A CEO with a history of building top-shelf companies and cultures.

I can report with certainty that A+ Players ask us about the top executive more often than B+ Players. That could be because true Top 10 Percent performers know they will close deals, hit their number, and earn big checks wherever they land. So, they’re thinking big picture. The CEO creates the environment that helps individual contributor sellers win, now and in the future. If you’re a sales leader, be sure to tout their accomplishments – IPOs/acquisitions, long tenures, leading well-known companies previously, patents awarded, and the person’s overall brand within the space. Just as the best CROs have “family trees” of high-performing reps who follow them from firm to firm, highly regarded CEOs have a history of producing kick-butt sales cultures over and over. Typical salesperson question: Does the CEO consider her firm a “product” company or a “sales” company?

10. Some form of financial reward tied to company success.

While cash is a major motivator for top sales reps, they’re also seeking opportunities that offer some form of financial reward tied to company success. This can take many forms, including stock options, Restricted Stock Units (RSUs), Long-Term Incentive Plans (LTIPs), profit-sharing, or some other form of equity in the company. When evaluating a new opportunity, top reps will look at these incentives and consider how they can benefit from them in the long run. They want to know that their hard work will be rewarded and that they have a chance to earn a nice payday if the company is successful. In 2022, 82% of the companies we represented offered one or more of these incentives, and they consistently had a leg up on competitive offers that did not include this perk. These incentives are not just important to the top reps but also to the company itself. They help to align the interests of the sales team with those of the company, and they motivate everyone to work together to achieve success. Typical salesperson question: Any specific reason they don’t offer equity or RSUs?

As you might imagine, RevsUp evaluates our prospective clients based on these 10 factors, so it’s quite fun to represent these firms to our talent network!

It’s tough to score perfectly across the board – believe me, RevsUp as an employer has plenty of room for improvement! –?but it’s important to acknowledge your firm’s strengths and weaknesses.

In our experience, the quality of sales talent each company attracts correlates directly with their performance against these factors.?

CEOs, VPs of Sales, and fellow salespeople … please leave your thoughts in the comments section!

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And if you’re looking to topgrade your sales team with the very best performers in your space, let’s chat: https://revsup.com/get-started/