Sales Hiring
Chapter 10

Sales Hiring

What to look for in sales candidates & how to assess them

Mark Roberge

Mark Roberge is a bestselling author and former CRO of Hubspot.

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It’s been two and half years since I published my book, The Sales Acceleration Formula, and over a year since I left my job as Chief Revenue Officer at HubSpot. A lot has changed in that short time period, but two things are still true for sales teams: hiring great salespeople continues to be the most important activity, and there is still no single formula that every company can apply to the process.

When I joined HubSpot in 2007, the company was a small startup with three people and a small office in Cambridge, Massachusetts. Within seven years, the company scaled to more than $100 million in revenue. One of the most essential parts of that journey was figuring out the process by which we hired salespeople. Every time I get up on stage to speak or meet with founders, they ask me the same question: What should I look for in a salesperson? As it turns out, this is a dangerous question, and I had to learn it the hard way.

data-driven-sales-hubspot@2x

Some of the first reps that I hired at HubSpot were top performers at their last company. I wined and dined them, took them to ball games, and even convinced a few to join our small startup. Yet, some of those “sure bets” didn’t work out. So what happened?

I learned early on that each salesperson is gifted in what I refer to as a “sales context.” There are reps who can close dozens of deals a week in a transactional SMB environment, and then struggle to close a single enterprise deal. Some reps were born to sell to marketers, and others can hardly speak the same language as the VP of Marketing on the other end of the line. Similarly, every company has its own sales context. Some have sales cycles that last multiple quarters. Others close deals on the first call. When the unique strengths of the salesperson align with the company’s sales context, it is a beautiful thing. When they do not, it becomes an uphill battle.

Fortunately for sales managers, success (and failure) in sales is arguably the most quantifiable compared to other functions (e.g., product, HR, marketing, etc.). Key performance indicators (KPIs) vary by company, but ultimately customer lifetime value is what determines success for every rep and sales team. The question is how to hire the people that can accelerate healthy revenue and beat their quotas.

At HubSpot, I spent many restless nights thinking about this question. Over the years I developed a process that helped us identify good candidates in the hiring process, evaluate them, and then feed that data back into the model. It was simple, but at times the insights that we gathered were counterintuitive. Below, I’ve shared that process in hopes of helping you build your own unique sales hiring process.


Step 1: Establish a theory of the ideal sales characteristics

First, I listed the characteristics I thought would correlate with sales success. For each characteristic, I documented a clear definition. What did I mean by “intelligence?” What did it mean to be “aggressive?” My intention was to score each candidate on a scale of 1 to 10 for each characteristic. Therefore I needed to define what a score of “1” versus a score of “5” versus a score of “10” represented for each characteristic. For each candidate, I summarized the results on an Interview Scorecard.


Step 2: Define an evaluation strategy for each characteristic

Once I defined the characteristics I was looking for, I needed a plan to evaluate candidates on each characteristic. What behavioral questions could I ask? Would I use role plays? Should there be an exercise for the candidate prior to the interview? How could I leverage reference checks?


Step 3: Score candidates against the ideal sales characteristics

Back in the early days of HubSpot, I simply filled out the Interview Scorecard after each interview. The process was not overly sophisticated. I used Microsoft Excel. (We were a startup—I needed to be “hacky.”) The key to the process was discipline, not sophisticated technology. I documented my findings and learnings as I went, and used them to constantly tweak my approach.


Step 4: Learn and iterate on the model while engineering the Sales Hiring Formula

A few months in, I had a handful of salespeople on board. Many were doing great. A few were progressing more slowly than others. By remaining disciplined in the process described in Step 3, I was in an optimal position to learn from these first hires and begin to understand our ideal hiring criteria. I was ready to engineer my company’s sales hiring formula. I simply went back to the Interview Scorecards for the top performers and asked myself the following questions:


  • Which characteristics do these top performers have in common? Are these characteristics predictors of success here at HubSpot? Once I identified them, I increased the weight of these characteristics.
  • Which characteristics do not seem to matter? Which characteristics do not predict success? I needed to decrease the weight of these characteristics or eliminate them altogether.
  • What am I missing? I had to think beyond the Scorecard and reflect on these top performers. Was there another consistent, meaningful characteristic to be found among them? If so, I had to add the characteristic to the Interview Scorecard and start rating candidates on it.

hubspot interview scorecard 02@2x

While we designed this process with scale in mind, it can work for almost any company no matter its stage or size. Recently I met with two founders of a SaaS company based in the northeast United States who told me that they wanted to hire a new breed of salesperson. Their idea was to only hire a very specific profile: someone who had graduated from a Top 5 MBA program (Harvard, Columbia, etc.) and then went to work for a top-tier consulting firm (McKinsey, Bain, etc.). The idea was that a high business acumen and intelligence level would lead to higher sales efficiency. But while the early results were promising, they eventually struggled with this profile. The reps weren’t accustomed to 50% of their compensation being variable, they hadn’t developed the same tactics that seasoned reps do, etc. Fortunately they were tracking their hires with a model similar to the one we used at HubSpot and were able to pivot their hiring strategy quickly.

Given the fact that every company has its own unique sales context, it’s natural to be surprised by what characteristics work out the best. After the first year running our model, we came to some counterintuitive findings: the characteristics that are traditionally associated with salespeople, such as aggression and strong objection-handling ability, had the worst correlation with success.

Once we had a large-enough sample size, we were able to start running regression analyses against important metrics like “revenue booked by rep.” We took the score each rep received during their interviews and compared them to their quota attainment and bookings later. Then we fed that data back into the model, which enabled us to weight certain characteristics more strongly.

canadidate assessment 01@2x

But we quickly learned that revenue and quota attainment weren’t the only metrics that mattered. Sales reps can potentially close deals by selling to the wrong customers or by using sales pressure tactics. However, those deals will usually churn fast. So an important metric for success was whether or not the customers had a long lifetime. LTV also takes into consideration the size of the monthly payment, which can indicate how well a rep prioritizes larger deals and manages their overall funnel to get the best revenue out of a given set of small and large opportunities.

Unfortunately, LTV wasn’t the perfect metric to measure either. One of the first things we realized was that it didn’t consider changes in rep behavior fast enough. For example, if a rep who was overselling deals—which leads to high churn—starts finding better customers, their LTV won’t start to go up until one or two years later. That’s a problem because the model will always lag reality.

This realization led us to develop leading indicators that could help predict LTV and future bookings by rep. Rather than look at a rep’s LTV, we began looking at things like the engagement of their customers within the product. We broke our product into 25 different features and then queried if the customer had used at least five of those features within the first 90 days. If they did, they were seeing the value of our product. If not, they were more likely to churn. This alone helped us get ahead of the problem by three or four quarters.

Once we had a model we were confident in, we learned that HubSpot’s best reps shared five characteristics:

  1. Coachability
  2. Curiosity
  3. Prior success
  4. Intelligence
  5. Work ethic

Here’s how we interviewed for each of those.


Coachability

Coachability is the ability to absorb and apply coaching.

Coachability was the most significant influencer of my hiring decision. As I think back to most of the rock stars we hired, their coachability was the personality trait that really stood out in their interviews. Evaluating this characteristic consumed the majority of my interview. Here is the three-step process I employed to evaluate this characteristic.

Step 1: Set up a role-playing exercise that models your buyer context

After some rapport-building questions at the outset of the interview, I would verbally set up a role play with the candidate.

Hiring Manager

“Jess, let’s do a role play. I am going to play the role of VP of marketing at a security software startup here in Boston. The company has about 20 employees. The marketing team is small—only two people. As the VP of marketing, I ended up as a lead in the CRM system, and I was assigned to you. As you reviewed the lead details, you saw that I had visited the HubSpot website last night and downloaded the company’s eBook on inbound marketing. We will role-play your opening call with me. Your goal is to do some light discovery and set an appointment to discuss my needs further. Do you have any questions? If not, please begin when you are ready.”

Step 2: Evaluate the candidate’s ability to self-diagnose

Once the role play was complete, I would ask the candidate to self-assess.

Hiring Manager

“Great work, Jess. How do you think you did?” Jess’s response to this question represented the first insight about her coachability that I collected. I wanted to see how reflective and analytical the candidate was about her performance. If the candidate simply stated, “I did great,” that was a bad sign. I wanted to see the candidate reflect on and analyze her performance. I wanted to hear specifics about what she thought she did well and what she thought she could have improved. Next, I would build on some of her observations. [Hiring Manager] “Great reflection, Jess. I agree with many of your points. You mentioned that you could have done a better job handling my question on SEO. If we could rewind to that section of the role play, what would you do differently?”

A candidate with a high degree of coachability is able to reflect, self-diagnose, and propose improvements to their weak areas. At this point, I would provide the candidate with the opportunity to demonstrate these abilities.

Step 3: Evaluate the candidate’s ability to absorb and apply coaching

At this point, I would begin some proactive coaching to see how she would absorb and apply the feedback. Absorb and apply: these two actions represent the essence of strong coachability. Some people struggle to even absorb the coaching, perhaps because they are poor listeners or simply don’t recognize the importance of feedback. Others absorb the information but struggle to apply it, perhaps because they are less adaptable or less skilled at thinking on their feet. I want to hire candidates who can both absorb and apply coaching.

Hiring Manager

“Okay, Jess, in every interview I provide one area of positive feedback and one area of improvement.”

Both components of this statement are important. If I offer only opportunities for improvement, the candidate might think she is bombing the interview. I run the risk of her freezing up on me, preventing me from evaluating her true abilities. By leading with a bit of positive feedback, I strike a warmer tone. After hearing a bit of praise, the candidate is more likely to feel comfortable and behave normally.

Hiring Manager

“I thought your opening rapport building was great, Jess. I liked how you broke the ice and created an immediate connection when you talked about your visit to Wrigley Field as a child. The area in which I would like to see improvement is the depth at which you seek to understand the prospect’s goal. Let me teach you how we deepen goal discovery here at HubSpot…”

I would then begin to coach the candidate. By this point, I would usually be up on the whiteboard, coaching her and also closely observing the candidate during this process. Is she glassy-eyed or is she taking notes and asking good follow-up questions?

After a few minutes, I would ask if the process made sense. I would request that she redo the role play, this time attempting to apply some of the coaching I had just provided her.

Now, most people really mess up the second pass. Their heads are spinning. They know the job is on the line. They are sitting with the VP of Sales. They’ve just received my feedback and must immediately apply it. In this situation, I am looking for effort, not perfection.

I will say that I have probably conducted well over 1,000 interviews during my six years in the head-of-sales seat at HubSpot. Across the full population of candidates I’ve screened, perhaps only five people absolutely crushed the second role-play attempt. Those who did so became absolute rock stars in our funnel. What’s the takeaway? Don’t expect perfection, but rather look for effort. If you witness perfection, hire that candidate at all costs! You’ve just spent 10 minutes with a candidate and witnessed meaningful improvement over that short time. Imagine how much progress you could make in a day, a week, a month!


Curiosity

Curiosity is the ability to understand a potential customer’s context through effective questioning and listening.

I have taught several classes on the subject of sales at MIT, Harvard, and other top universities across the United States. One of my favorite ways to start the class is to ask the students, “What makes a great salesperson great?” The most popular answers are consistent across venues and audiences: “aggressive,” “convincing,” “great presenter,” “money hungry.”

I don’t think anyone has ever given me the answer I am looking for. Great salespeople are naturally curious. They ask great questions, listen intently, and probe into points of interest.

Great salespeople ask questions of potential customers in a manner that does not feel interrogative. Instead, potential customers feel like great salespeople are genuinely interested. After all, if the salespeople are truly great, they genuinely take interest in the responses of their prospects.

Great salespeople educate potential customers through the questions they ask. Their questions are thought provoking and elicit introspection. “You know, nobody has ever asked me that before. Now that I think about it …”

Great salespeople quickly build trust in order to earn the right to ask personal questions and to receive honest answers in return.

Great salespeople seek to understand customer goals, aspirations, fears, and struggles—all through tactical questioning.

Students often ask me, “Mark, how can I prepare myself to be a top performer in sales?” I offer the following advice: the next time you are at a wedding reception, a school networking event, or a party on a Friday night, approach a stranger and ask them questions. See how long you can question that individual without mentioning anything about yourself. If the individual walks away from the conversation feeling interrogated, you need more practice. If the individual walks away thinking, “Wow, that was a really smart and interesting guy,” you are on your way to becoming a great salesperson.

So how do we test candidates for curiosity? There are many areas in the interview process, but I will highlight two especially important opportunities.

The first test of curiosity happens the moment I meet a candidate in the lobby. “Hello, Jess. My name is Mark Roberge. Thanks for coming in today.”

Does the candidate start with a question? Does the candidate ask me about my day? Did the candidate research my background and does she take the opportunity to reference an observation from her findings? Based on my responses, does the candidate follow up with smart, open-ended questions to learn more? If all of these things are happening, then this interview has started really well for me (and for her).

The second test of curiosity occurs during the role play. Let’s use the same role play that I set up in the previous section on coachability.

Ring Ring.

MARKETING MANAGER

“Hi, this is Mark.”

CANDIDATE

“Hi, Mark. This is Jess at HubSpot. Did I catch you at a bad time?”

MARKETING MANAGER

“I have one minute.”

CANDIDATE

“Great. I am not sure how much you know about HubSpot. We have an all-in-one marketing platform that helps companies get found online and convert visitors into leads and customers using your website. We have worked with Company X and Y in your industry. I am calling to see if you would be open to a 10-minute call to assess your company’s online visibility.”

Disaster!

Let’s try that again. This time, Jess will be far more curious.

Ring Ring.

MARKETING MANAGER

“Hi, this is Mark.”

CANDIDATE

“Hi, Mark. This is Jess at HubSpot. Did I catch you at a bad time?”

MARKETING MANAGER

“I have one minute.”

CANDIDATE

“Great. I noticed you downloaded our eBook about generating leads on Facebook. What specific questions did you have about Facebook marketing?”

Yes!

MARKETING MANAGER

“Oh, jeez. Um. I was just doing some research. I think I was looking for examples of B2B companies that had seen success using Facebook for business purposes.

CANDIDATE

“Great. I am happy to share some of those success stories. Have you run any Facebook campaigns yet?”

Yes!

MARKETING MANAGER

“I have.”

CANDIDATE

“How did they go?”

YES!

MARKETING MANAGER

“Okay.”

CANDIDATE

“Okay? What do you mean?”

Yes!

MARKETING MANAGER

“Well, we did generate a lot of new emails from the campaigns. Unfortunately, I am not sure the people we are attracting are really qualified for our service.”

CANDIDATE

“Interesting. What types of people are qualified for your service? What types of people did the Facebook campaign attract? ”

Yes!

Does the candidate lead with great questions? Or does the candidate “show up and throw up,” as we say in the industry?

Does the candidate ask about the specific areas the prospect cares about? Or does the candidate bore the prospect with her company’s elevator pitch?

Curiosity is the ability to understand a potential customer’s context through effective questioning and listening.


Prior Success

Prior success is a history of top performance or remarkable achievement.

It is probably the easiest characteristic to evaluate, especially if the candidate is coming from a reasonably sized sales force. It is the most objectively measurable of the “big five” traits.

Hiring Manager

“I noticed you were an account executive at your last employer. How many account executives were there at the company?”

Candidate

“125.”

Hiring Manager

“Where did you rank?”

Candidate

“Six.”

Hiring Manager

“Wow! Impressive. What metric is that rank based on? Bookings? Attainment?”

Candidate

“Bookings.”

Hiring Manager

“And the rank is based on last quarter or all of last year?”

Candidate

“All of last year.”

Hiring Manager

“Very good. And your references will verify that performance?”

Candidate

“Of course.”

I am looking for top 10 percent. If the candidate falls outside of that range, the candidate really needs to rank extremely high on the other key characteristics in order to earn an offer letter from HubSpot.

Evaluating prior success becomes more challenging when the candidate does not come from a reasonably sized sales organization or does not come from sales at all. In these cases, I evaluate prior success through other activities in the candidate’s life. How did the candidate perform academically in school? What was her class rank? What were the candidate’s standardized test scores? Was the candidate a standout performer on a varsity sports team? Was she the captain of the team? Perhaps she contributed to a major championship? Was the candidate a member of student government or a leader of an extracurricular organization? If the candidate is transitioning from a nonsales background, how did the candidate differentiate herself from her peers in her current or former role? What made her special?

On the HubSpot team, we had an Olympic gold medalist. We had a cello player from the Portland Symphony. We had a former comedian who was featured on Comedy Central. These people pursued their life passions with exceptional vigor and performed at a top percentile level. These people are likely to bring that same passion and competitive drive to their role in sales.

Prior success is a history of top performance or remarkable achievement.


Intelligence

Intelligence is the ability to learn complex concepts quickly and communicate those concepts in an easy-to-understand manner.

Not every sales team needs intelligent salespeople. For example, in a commoditized buyer context, I would bet that work ethic, rather than intelligence, is the superior predictor of success. However, in the HubSpot buyer context, intelligence proved to be a strong predictor of sales success. In retrospect, I believe intelligence was a key trait because our industry was evolving so rapidly. For context, Twitter was a garage project when we first started selling HubSpot. Just seven years later, it is a $25 billion technology titan. That should give you a sense of how quickly the industry was transforming in the late 2000s. Our salespeople needed to keep pace as the industry around us took shape. They needed to understand new concepts and communicate to our target customers exactly how those concepts impacted optimal marketing strategies. Because most early-stage companies operate in rapidly evolving industries, I expect that intelligence would be a predictor of sales success in their buyer contexts as well.

I tested intelligence by effectively commencing HubSpot sales training during the interview process. I exposed candidates to new information early in the interview process and observed their ability to absorb the information and communicate it back to me at a later stage in the process. For example, at the end of my first phone screen with a candidate, I would send her training materials on the concepts of inbound marketing, SEO, blogging, and social media. I would ask her to learn the material before our next interview. Then, I would be sure to reference the materials in our next role-playing session.

Here’s an example of testing for intelligence and information retention:

Mark

“Jess, I noticed on your website that you offer SEO services. I always wanted to better understand how I could improve my business’s ranking in Google searches. Could you explain how I might go about doing that?”

Her response would offer me a first impression of her performance on this characteristic. To reinforce my earlier point, I am trying to understand two things here. First, how well did she understand the concepts to which I had I exposed her? Second, how well did she communicate those concepts back to me in a simple manner? I would always ask follow-up questions until I eventually stumped the candidate. The deeper I was able get on a topic before her responses suffered, the better it meant she was performing.

Intelligence is the ability to learn complex concepts quickly and communicate those concepts in an easy-to-understand manner.


Work Ethic

Work ethic is proactively pursuing the company mission with a high degree of energy and daily activity.

Work ethic is probably one of the most difficult characteristics to evaluate. These are the three techniques I use to gain insight into each candidate’s work ethic.

  1. Observations during the interview process: A lot can be learned by simply observing a candidate’s mannerisms and behaviors during the interview process. This is especially true for assessing work ethic. How quickly did she return phone calls? How quickly did she turn around deliverables (such as her resume, her assessments, or her feedback from the interview)? Did she push the pace of the interview process or were we pushing her? All of these observations provide insights into the candidate’s work ethic.
  2. Reference checks: Conversations with former supervisors or peers represent opportunities to assess the candidate’s work ethic. Don’t ask, “Did the candidate work hard?” Instead, ask the following questions: “Here are four characteristics that may describe a candidate: coachability, curiosity, intelligence, and work ethic. Could you please rank those characteristics from strongest to weakest for this candidate? Why did you rank these characteristics in the order you did?”
  3. Behavioral questions: I often use behavioral questioning to explore the level of rigor with which the candidate approached her responsibilities— for example, “Please tell me about your typical work day or work week. What are some of your must-do activities?”

Work ethic is proactively pursuing the company mission with a high degree of energy and daily activity.


It’s worth pointing out one more time that these were the characteristics that made sales hires at HubSpot successful because they fit our sales context, not because we identified some law of sales hiring that applies to everyone. At a company of a different size, or one that sells pharmaceuticals, the criteria might vary widely. The point of all of this is to show the process and our methodology, and hopefully inspire a few sales teams to develop their own.

I was lucky enough to join a company like HubSpot that treated almost every aspect of business like a science experiment, and hiring was no exception. From the day I joined until the day we IPO’d, we followed the same process: we started with a hypothesis, we tested it, and then we iterated.

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