What to Expect When Interviewing for a Sales Management Job in Tech
Sales management positions at fast-growing companies are so highly coveted that some candidates are willing to perform acrobatics just to stand apart from the competition.
When Brett Kirhofer, who’s been a sales manager at Hireology since 2018, asked one candidate what made him more qualified than the 20 other applicants, the candidate took it as a physical challenge.
“He gave a short explanation, stood up, moved the chair to the side and did a standing backflip right in front of me,” Kirhofer said.
So did it work?
“I did not hire him,” he said. “But the backflip was very impressive.”
Feats of strength and agility may not be prerequisites to get hired as a sales manager, but the role is indeed demanding. Like all good individual-contributor sales reps, the right candidate must fear no quota, but also know how to lift colleagues to their level of success. And, of course, it’s critical that interviewees know how to make their skills and experience apparent.
We spoke with Kirhofer and three other Chicago-based sales managers and directors about questions candidates can expect to field, hypotheticals they should be prepared to consider, red flags for which to be alert and other general advice on how to sell yourself, short of leaping through the air.
Below are eight common questions — plus one of our panelist’s favorite wild cards — that candidates should prepare to encounter, touching on everything from data to people management styles to managing former colleagues.
After that, our experts offer six bits of general advice on how to approach the interview, including what to wear and how to talk compensation.
- Brett Kirhofer, sales manager at Hireology
- Dathan Brown, sales manager at ActiveCampaign
- Ashley Lochen, sales manager, market development at DocuSign
- Brian Paladie, director of sales at Upwork
“Why is now the right time for you to become a manager?”
Sales Manager at Hireology
That’s an important and common question that you should be ready to answer well. I’d say: “Six months ago I was still performing at a high level as a rep, but I didn’t have a good enough understanding of the business. So I’ve focused on that over the last six months, understanding how different teams and departments work and how it all adds up together. Now that I have a much better understanding of that, I feel ready to take on the next challenge and can offer good ideas that can increase revenue and take us to where we need to be.”
“How would the top performer on your team describe you?”
Director of Sales at Upwork
Typically you’ll hear, you know, a good advocate. I am involved on the higher-level deals and I’m good at setting strategy. But I let them control their own destiny because they’re showing great results.
But then I follow up with a related question: “How would your lowest-performing rep describe you?” That’s intentional, because most people have a tendency to highlight the positives. You get a different perspective from somebody who’s struggling and may not be communicating well with their manager. That lets the candidate reflect in the moment on where their gaps may be. They may not really be fully thinking about this in a 360-degree perspective of how everybody on their team is feeling about the relationship that they have with their manager, or the person who will be moving into a manager position.
“How will you handle managing former colleagues?”
Kirhofer: I was promoted internally. So they said: “You’re not the only person on your team interviewing. If you get the role, how would you gain credibility from those who saw you as a peer, and now you’re their boss?” What hesitations do you have about managing that person?
You have to make clear that, on day one, you’ll set the expectations and vision you have for the team. On my first day as manager, I called an all-team meeting at the end of the day and said, “There’s a lot of things we’re doing well as a team that I want to continue, but I want to make XYZ changes. I was once your peer, and now I am a manager, but that doesn’t mean I won’t be in the trenches with you making calls, being on demos. If you have any questions or hesitations, come talk to me.”
It’s so important from the onset to set the right expectations and establish processes.
“Are you comfortable analyzing data?”
Kirhofer: Being comfortable with data is important, but what’s most important is the ability to tell a story of what the data can accomplish. You have closing percentages, call-to-set ratios, average selling prices. But how do you build a plan to drive revenue based on those data points?
In my interview, I talked about how, at the time, I felt that we didn’t truly understand the full funnel — how many calls result in a meeting being set, how many meetings set result in actual meetings, how many meetings lead to deals. So part of the focus of my first 90 days was to get everybody to understand and work towards those metrics. A better understanding of metrics and conversion means they can see for themselves what truly needs to happen in order to go hit quotas.
Sales Manager at DocuSign
You have to be able to read historical data as it pertains to properly forecasting new business, but also empowering your sales teams with information that’s going to drive impactful business decisions. A big buzz phrase in the tech industry right now is “data-driven decisions.” How can you use data to drive important and impactful business decisions?
It’s more prominent now than ever, as the tech environment gets more and more competitive. How are you using your data to not only make your business stand out and explain what clients can gain with your software, but also to help prove return on investment, and show why your solution makes sense over a competitor.
“Why do you want to manage people?”
Sales Manager at ActiveCampaign
What about having a team will motivate you? That’s something a lot of folks who are moving forward in their careers don’t necessarily have the right answer to. They’ll say, “Oh, this is the next step.” But you really need to be people-focused.
If you just want more money, that’s very much the wrong reason to go into management. That’s a great reason to stay a sales rep — go sell more. You’re going to need to legitimately care about a team.
“How will you turn a C player into an A player?”
Lochen: It’s a big thing that, as a sales manager, you deal with on an almost a daily basis.
It would be ideal if you had 10 top-performing reps who smashed their numbers every quarter. But it’s not likely. People learn and adhere to change differently.
What’s made me most successful is asking questions rather than issuing commands. It’s not a total choose-your-own-adventure, but more along the lines of: “Hey, what do you think you should do? What are your thoughts on doing it this way? And let’s work together to put together a resolution to get you where you need to go.”
“What makes a good leader?”
Brown: Think about your experience working with your previous sales managers: What went well and what did not?
Leading well comes back to communication. I would talk about knowing where you fit in, where your work is going well, where it can improve and your ability to make a plan to drive the business forward. Mastering that communication piece, whether you’re working with your sales reps-to-be or your sales director or VP, makes a big difference in how successful you're going to be.
“Are you an idea-generator, a process-facilitator or a solution-finder?”
Paladie: Not a typical question, but one that I love. There’s no right answer, but it gives a sense of their self-reflection and how they’d slot into the team. Because if you over-represent a single profile, you’re less likely to be successful. You want complementary assets.
I try to find out how that person sees themselves, then compare that to the people already in leadership to see how we’re building the team as a whole. If you have a bunch of innovators, great, but who’s executing on that? If you only have process people, where were your ideas coming from?
“In six months, how will you know you’re successful?”
Kirhofer: That question surprised me a bit because sales is so metrics-driven: What’s our target, and did we hit it? That pretty much tells whether you’re successful. But from a management perspective, I now understand it more.
Yes, it’s great to hit the number, but you also have to look at how you hit the number. Did you have one rep who blew it out of the water but the other reps failed? That’s not ideal. I would measure success along the lines of: Are all my reps — not just us as a team — performing consistently month over month, quarter over quarter, and year over year?
Brown: As a manager, the numbers are still heavily in play because you have your total number, which is reflective of all the people in your seats. Each seat is generating a certain amount of revenue or number of qualified leads. Or you’re given a more aspirational goal. So you’ll still have a big numerical component.
Beyond that, the more qualitative piece comes into play for how you motivate your reps and get their different aspirations and talents moving in the right direction. That includes what kind of program you’re going to run, onboarding, ongoing training and potentially spiffs or compensation. Keeping all those pieces together helps drive the numbers that you need to hit.
Of course, landing a sales manager role isn’t just about answering questions. We asked our experts about other things to keep in mind as you prepare for your interview.
Watch for red flags
Lochen: It’s really important to get transparency about the organization’s growth and see that there’s a clear cut-path for your career.
Advancement is big. It’s important that people demand the understanding of where they’ll fit into the grand scheme in year one, three and five, if not longer. And understand the company’s vision and growth goals, as well as its acquisition strategy. Sometimes that information is proprietary, but it shows the employer you’re doing your homework and invested in the company. If someone’s not prepared to give you at least an educated guess, that could be a red flag.
Kirhofer: What’s your plan of growth for the next three years? Are they slowing down? That might be a red flag. And ask what percentage of sales reps hit their monthly and quarterly targets. Is it lower than it should be? You might be going into a position where you’re not making much money because the reps aren’t hitting quotas. Am I facing a long uphill battle, or do the reps maybe just need a bit more structure?
Brown: Trust your gut. If something feels off, evaluate that. Ask questions that will help you get more information about your misgiving. When you’re interviewing, that is when they’re putting their best foot forward too. Obviously we want to put our best foot forward as candidates, but when you look at it from a business perspective, they need to do that too.
Kirhofer: Understand the market. If I’m already a sales manager in Chicago moving to another sales manager position, I’m probably expecting at least the median, if not more, because I have experience. But coming in as a new manager, I wouldn’t necessarily expect that.
Get more details. Do we do a performance review every year? And if so, is it a 5 percent bump? Is it an arbitrary percentage? What’s the figure based on?
And take into consideration what you make as a sales rep. If my on-track earnings are $100,000 [as an individual contributor], but it’s $105,000 as a sales manager, that’s not that much more money for a lot more work and a lot more responsibility. What percentage of on-track earnings is guaranteed base salary versus a harder-to-predict variable compensation?
Lochen: Do your research. A lot of compensation information can be found publicly. I always tell people, ask for 20 percent more. It’s better to shoot your shot, aim high and then come back, rather than aim low and have nowhere else to go.
People sometimes assume that compensation will be the same [in a lateral move]. But it may be equal pay from a paycheck standpoint, but not in benefits and equity. Ask those questions up front. It’s harder to negotiate at the end. There’s always room for negotiation. Our clients negotiate with us all the time; we have every right to negotiate back.
Brown: Be realistic in terms of company size. A company that sells a product that lacks high dollar value usually doesn’t have salaries in the high range. If they have a longer or more complicated sales process, sometimes those salaries are more toward the top of the range. But come in prepared and willing to defend the value you’d bring.
Look the part
Kirhofer: We all know how relaxed tech companies can be. Most of my reps wear jeans and T-shirts, which is totally fine. But if you’re going for an internal promotion, treat the interview as an [external] interview. I showed up in a suit and tie. I wanted to treat it like they didn’t know me and be as professional as possible.
My counterpart showed up in jeans and a T-shirt. He thought, “You guys see me in this every day, why should I change?” I think that spoke volumes to leadership about how serious he was about the role. Dress up, be professional, have your resume, and don’t assume that just because you work here, you have a leg up. It’s not going to be the reason you do or don’t get the job, but it’s going to contribute.
Expect to revisit a past deal
Lochen: In sales, you’re always playing back the good, the bad, the ugly — the wins and the lost deals.
Even as a manager, I’m asked this. Who are you working with in the process? What roadblocks did you incur with the client? What key takeaways did you gain? And how do you scale that learning across the organization?
People appreciate an ability to be vulnerable and to admit when things didn’t go perfectly. Especially in sales, you’re selling yourself. But people do look for candidates who are open to constructive criticism and able to admit their faults. You want confidence in the interview, of course, but you also want to see how people handle difficulties.
Think of the interview as a talk between colleagues
Lochen: So many people come into interviews super nervous. Think of it more as just a conversation with another person in your industry, and less as someone judging your jobs and accomplishments. People buy from people they like, and people hire people they like — it’s no different. That helps take some of the pressure off a stressful situation.
Finally, don’t wait for the title before you start leading
Lochen: For reps on my team who are interested in becoming a manager one day, I strongly urge them to mentor new sales reps. You don’t have to wait until you have a manager title to make someone else more successful. That also gives you a taste of whether you like developing people. Do you like showing people the ropes, and offering coaching and feedback? Some people who I’ve seen become great managers started doing that on a small scale — taking on some of that burden to make someone else better. That makes them better at their individual contributor roles, but it also prepares them to be sales managers.
If you and Candidate B both have an average of 100 percent attainment, they’re going to look at other factors outside of numbers. What leadership characteristics did you establish? What projects did you do a bit differently that scaled out to the organization?
We’ve done the sales. Awesome. What makes you different from the person next to you?