Over the last 16 months, I’ve worked with approximately 40 software sales leaders, and I’ve probably spoken with 120. Between 2002 and 2015, I hired about 250 salespeople myself.

A quick disclaimer: my client base is mostly Mar-Tech / Sales Tech companies with between 35 and 2,000 employees, so by all means this feedback is not representative of all software sales jobs.

By necessity, this post is also a bit of a reflection on resumes. I truly believe a great sales resume is simply a reflection of your financial accomplishments, and other achievements that sales leaders value. As such, here is a sample resume (OK, it’s my old resume). It’s actually a one-page resume, with a number of appendices – a “sales portfolio”, if you will. You might like the format, you might hate it. But it does illustrate one way that sales candidates can communicate the information outline below.

When VPs of Sales are looking to hire Top 10 sales executives, here are the factors they tell me are most critical. And yes, these are listed in order of importance. So, every time a hiring manager declared a specific factor as important, I gave it a (loosely tallied) point.

1. Your Financial Performance Over the Last 5 Years

Believe it or not, it took a lot of arguing (in my head) to decide between Performance Metrics and Tenure for the top spot. (Feel free to debate the list’s order in the comments). But guess what, if you’re someone who can certify that you consistently crush quotas and rank among the top 10 percent among your peers, that solves many problems! Of course, there is gray area galore. Out of the last 10 years, you’ve exceeded quota 5 times, 10 times, or most likely, somewhere in between.

Any line in your resume that describes standard job duties – that is, the same stuff that anyone with the same title would do every day – is extraneous. So delete all the “built relationships” … “made cold calls” … “used Salesforce CRM” and use that precious real estate to detail your accomplishments:

  • Annual quota and achievement against it.
  • Ranking among your peers.
  • Your last three W-2s.
  • Total ACV or TCV generated.
  • Names of companies you’ve closed with business with (i.e. logos).
  • President’s Clubs, promotions, other notable awards.
  • Unique and interesting non-sales-related contributions you’ve made to the company.

When I send a hiring manager a clean, one-page resume that details these accomplishments, year after year, that candidate gets an interview, and quickly.

For interviews, be prepared to discuss your performance metrics in great detail, as well as 1 or 2 specific deals. Pick large ACV and/or complex and/or interesting deals. Size of the company doesn’t matter as much.

  • How did you generate the lead?
  • Who did you engage with throughout the sales process (titles)?
  • What obstacles did you overcome?
  • What were the deal specifics (ACV, term)?

2. Your Tenures Over the Last 10 Years

Yes, this topic could be 2,000 words on its own, but I’ll spare you. I see one concept driving all conversations about tenure: that a rep’s recent choices around tenure are predictive of what a VP of Sales can expect if she hires this rep. I tend to agree with this thinking. If you’ve just completed your third consecutive 24-month tenure, what evidence do we have that “this one will be different”?

And remember, sales leaders really want to hear why you left the last few roles, so you should have strong, honest narratives around each recent departure. Big caveat: leaving because of a positive transaction (i.e. company sold or IPO) is typically viewed as neutral or positive, regardless of the duration of your stay.

Here are the most common situations I encounter, and some ideas on positioning.

A. 8 to 10 consecutive years at the same company: This profile generally gets strong marks. It indicates both loyalty and, almost by definition, strong financial performance. The main concern I hear is, “How will this person adapt to a new company / culture / product? They’ve been with ABC Company for so long.” But you’re certainly not a rep who jumps at the first sign of trouble.

B. 2 to 3 companies over the last 10 years. This might be the sweet spot, as you’re talking about average tenures of 3 to 5 years. There were probably down years among the last 10, yet you pushed through and produced. If one or two of these companies went through big growth during your residency (i.e. you grew $5 million to $50 million over 4 years), that’s as good as it gets. Your new VP wants that same growth trajectory, and wants to hire people who know what it feels like to get there.

C. Multiple 1-year stints over the last 10 years, with some decent engagements in between. Timing matters on this one. If you’ve just come off two consecutive 12-month stays, it’s going to be challenging for a staffing agency to represent you. If you’re currently 12 months in your current role, but the previous stint was 3 years, that’s a different narrative.

D. 3+ companies over the last 4 years. Companies will absolutely hire reps in this category, but they won’t pay a staffing agency fee. Being labeled a “job-hopper” is as painful as it gets for an AE, and I truly empathize. I had two consecutive 10-month stints myself. In 2012 at Baynote, financing issues caused our owners to slash the company from 87 to 40 people – all C-Levels and salespeople were released on the same day. 10 months after that, I left an awesome Individual Contributor role at Experian to take a leadership role with my former Baynote boss. If I had started to actively look at that time, I assure you I would have heard crickets from staffing agencies.

My best advice here: if you can handle it, stay at your current company for a full 24 months. The difference in perception between a 16-month tenure and a 24-month tenure is wider than you believe.

E. Many sub 12-month stints, and probably more that aren’t on your resume/LinkedIn. Sorry to say, but sales is probably not your calling.

I recently presented an AE who had put up very good numbers, but had been with 4 companies in 7 years. The CRO’s email to me: “I do like the background and you have found the right composition. I worry that he hasn’t been anywhere long enough to prove value. Unlucky? Maybe. We like lucky reps.”

3. Success Selling to the Same Buyers

I’m working on a separate post about how to switch your sales focus, because I hear from two dozen people a week who are looking to do this. Just like overcoming job-hopping, switching focus can be done fairly easily if you’re really good – but a staffing agency is not the best route. My clients are all members of the Chief Mar-Tech list, and I’m required to present candidates who have generally sold the same stuff, to the same buyers.

I assume that other specialty sales staffing agencies (Big Data, Security, Hardware, FinTech, etc.) face similar restrictions.

I’ve certainly presented a number of “DNA” candidates; that is, quota killers who just haven’t specifically sold into marketing and sales leaders. But over these 16 months, I haven’t placed a single Account Executive who didn’t have documented success selling to the same buyers that my client sells to.

4. Business Acumen and Critical Thinking Skills

One of my favorite clients specifically looks for “CIA” reps – Curious, Intelligent, Active. I love this! The main way these attributes are communicated is through your interview performances, but here are two others to consider:

  • Share long-form writing samples. Have you ever written a business plan? Sales plan? Creative prospecting email? Blog post? 30-60-90 Plan? Are they any good? If so, make them part of your portfolio! In 1998 I wrote a 50-page, MBA-quality business plan to launch a new division, complete with deep research, P&Ls, competitive analysis, etc. I left that role before the plan was ever implemented, but the business plan itself helped me land my next three jobs.
  • Share your reading list. This is a reflection of your intellectual curiosity, and guess what? The people you’re interviewing with have probably read many of the same books.

5. References and Recommendations

I’m genuinely surprised that more AE candidates don’t promote their network of referrals and references early and often in their search process. As you can see on the sample resume, I pulled a few from my LinkedIn page and added them as a resume appendix.

For privacy reasons, I removed their phone numbers and emails from the resume, but contact information was included on my official resume. That’s a pretty strong first impression, in my opinion: “Here are some people who will validate the performance claims I’m making, and by the way, go ahead and call them today.”

6. Prospecting Skills

This is a classic back-and-forth. Reps want to hear that a company has strong lead-gen/demand-gen/marketing operations, and hiring managers want to hear that reps generate their own leads and don’t rely on outside lead sources.

Except for special cases, Enterprise reps should expect to self-generate about 75% of their new-business opportunities. Can you make $300k a year using only SDR leads? Yeah right. So highlight your prospecting methodology – both art and science – when interviewing. I wouldn’t wait for the hiring manager to bring this up – reps with a passion for prospecting can shoot up the list.

7. Location

Truthfully, my customers would rank this in the top 3, while I would personally rank it towards the bottom. I always tried to hire the “Best Available Athlete”, as long as their home address was in a Top-20 metro area and they were fine with travel. Some of my best reps ever were based in Minneapolis, Charlotte, Phoenix, Denver, etc.

Based on the concentration of Fortune 1000 / IR 1000 companies in New York, Chicago, and the Bay Area, it’s certainly a travel advantage to have reps nearby. But it’s a frustration of mine when A+ Players in these “second-tier” cities are passed over for B+ Players in a Top-5 metro areas. I mean, 75% of sales activities (at least?) are conducted via email, phone, WebEx, ClearSlide, etc.

What Didn’t Make the Top 7?

My observation is that excellence in the following areas can shoot you to the top of the pack, while significant weaknesses here can submarine your chances.

Cultural Fit: Definitely important, and no one wants to hire a jerk. But you know what’s amazing? Reps who hit 115% of quota year after year invariably become great cultural fits! I’ve hired Challengers, Lone Wolves, Hard Workers … there’s more than one way to get to President’s Club, and my clients are actually seeking diversity of background, opinion, and culture. Whether your role is office based or remote also plays a factor here.

Presentation Skills: I lost three placements in 2016 because of poor presentations / Sales Challenges. Truthfully, sometimes it was poor instructions from my client, sometimes it was poor execution by the rep. Regardless, you present for a living, so you should be able to kill this exercise.

Your Day-to-Day Job Duties: this is the scourge of sales resumes, as I hinted at above. Here’s a simple test for a resume bullet point. Does this bullet describe an activity, job duty, or responsibility that everyone with the same title is expected to do? If so, leave it out, or better yet, replace it with an accomplishment. Examples: building pipeline, prospecting, creating Powerpoint presentations, conducting phone and face-to-face client meetings, etc. etc. Who cares? Of course you did all these things. More importantly, what financial accomplishments did these activities lead to?

If you shine in these seven areas (or most of them), be sure to highlight them in your resume and during the interview process.

You’ll be well on your way to finding your next great sales role!

About RevsUp

What makes RevsUp unique?

  1. All Sales, All the Time: Our company was co-founded by two experienced software salespeople, and we exclusively employ former President’s Club salespeople – no exceptions to this, ever.
  2. Certified Top 10: We only work with Candidates who are consistently ranked in the Top 10 Percent among their peers, and we validate this through networking/reference checks.
  3. Integrity Above All: We don’t sell Jobs to Candidates, and we don’t sell Candidates to you. We simply make the match.

While we would love to help everyone we connect with, our firm focuses exclusively on SaaS salespeople who have 5+ years of experience working for companies on the Chief Mar-tec list.