B2B Sales Hiring Tips and Trends from the Trenches

Devon-McDonald by

Learn how companies are successfully scaling their sales teams with the latest B2B sales hiring tips, tactics, and approaches proven to work.

Carlie_circleLast year, OpenView’s talent team hired over 100 people for our portfolio, and over 30% of those hires were sales roles. The woman behind the majority of that success is Senior Talent Specialist, Carlie Smith. Given the high demand from the portfolio, Carlie is now nearly 100% focused on sales hiring for our investments.

Most companies at the expansion stage are focused on finding the absolute best sales talent to scale their organizations — and finding it difficult to do so. To help you remove some of the friction from your sales hiring process, I asked Carlie to share some of her best tips and insights on how companies can efficiently and effectively add talent to their teams.

Carlie, what level of sales hire do you find the portfolio companies struggling with the most?

Honestly, it’s the inside sales reps with 1-2+ years of closing experience within the software space. I’m specifically seeing companies in the Boston and San Francisco Bay area markets having the most difficulty hiring in this area. That’s not too surprising given how competitive those markets are.

What are the three questions that you will always ask a sales candidate in your first conversation?

  1. What is your quota/attainment? I ask this for every position and company in the candidate’s history. It’s important for a potential hire to have been successful in different environments, whether that’s at a different company, under a different manager, or selling a different product.
  2. What is your motivation for taking my call today, and for looking at new opportunities? I always ask this question twice. The first time — after I have walked through the opportunity to the candidate. The second time — after they have given me a deep dive of their experience. I almost always get two different answers, the first a high level view and the second real insight into why they are motivated to leave. Asking this question twice allows me to dig deeper into a candidate’s real motivation as well as their thought process when it comes to potential career moves.
  3. What is your prospecting strategy? Given that I’m mainly recruiting for hunters and reps who are focused on new business, I want reps who know how to prospect and are aware of the downside of relying completely on inbound leads.

What tactics have you seen the companies able to quickly hire the best sales people using?

The best tactic is to always be recruiting. Jeff Hoffman says it best — sales hiring should be treated no differently than building pipeline. After all, just like your best prospects and customers, top sales performers can leave your business at any time, and sales leaders must be prepared to immediately fill those holes as quickly as possible.

To that end, sales recruiting is really all about building a solid network and being able to actively rely on that network for both candidates and referrals.

Companies doing it right are not relying 100% on a recruiter for building the team. The entire sales team from top to bottom is constantly making connections, whether it’s meeting future potential candidates at a trade show or paying it forward via networking and introductions.

What is the best interview process you’ve seen for moving candidates along swiftly but thoroughly?

First and foremost, the best sales interview processes are consistent and repeatable.

Second, every member of the interview team needs to be aware of how they are involved in a search, and there needs to be buy-in around their role within the interview process. If you have that, you can move through the entire process quickly and efficiently, while at the same time being thorough.

It’s really the buy-in that counts, knowing that their time is needed in order to make the hire. I’ve seen processes that have five steps take a shorter amount of time than a process with three steps, simply due to not having the proper buy-in from the interview team and the interview team not having a sense of urgency to get candidate interviews on their calendars.

The specific interview process will vary depending on the type of sales role. For instance, the interview process for an inside sales rep will lean toward more phone screens than a field sales role, given the nature of the position.

With sales, the interview team should include the hiring manager who will directly manage the rep, the VP Sales, as well as relevant managers and peers. If it’s a field sales role, I’ve also seen successful interviews that include the head of sales operations or sales engineering.

Finally, there should always be references. Ideally, the hiring manager will conduct reference checks, as it’s an opportunity to uncover new information on a candidate, discuss the best way to manage a candidate, etc. Reference checks should include past managers, a peer, and a client reference, if possible. Here are a couple of free reference interview guides to help walk you through them.

Comp is obviously a driving force for sale people. What’s the best comp structure you’ve seen a company offer in terms of structure?

The best compensation packages are the ones that incentivize top performers and pay out variable comp on a curve. These packages go hand-in-hand with realistic sales goals. Remember, sales reps cannot make money unless the quota is a realistically achievable goal. That said, the best sales reps are the ones who ask what the accelerators are, not those who are worried about what making 70% of their number will get them.

In today’s market, companies also need to be competitive on base compensation and cannot rely solely on accelerators and great kickers to sell candidates on the role.

Do you recommend having a candidate deliver a presentation in the final rounds?

I do. Here’s one quick example. Have the candidate prepare and present a deck in reaction to the following scenario:

Two weeks ago, your lead qual team made headway with the (insert potential customer company). The lead qual rep was able to speak with the (insert buyer persona A) for about 15 minutes and give a brief overview (insert your company). The conversation went well enough that (insert buyer persona A) was able bring (insert higher level decision maker) to join me for a 20 minute presentation/executive overview.

Essentially, (insert buyer persona A) needs you to help convince her manager to allow her to move forward in discussions with you and bring in the rest of the team for more technical and deeper discussions as next steps.

Feel free to use whatever presentation materials you’d like to prepare for the call. If you have any questions, please feel free to reach out.

This type of presentation will require a candidate to do research on your company as well as a potential customer company, and put together a slide deck. Here’s what you’re looking for:

  • Did the candidate take the time to prepare a thoughtful presentation that addresses the customer’s specific needs and challenges?
  • Did the candidate start the presentation with an overview of the agenda and goals to get buy-in from you (the prospect)?
  • Was the candidate asking questions during presentation to keep you (the prospect) engaged?
  • Did the candidate sound confident, knowledgeable and professional throughout the presentation?
  • How did the candidate handle objections?
  • At the end of the presentation did the candidate ask for the business?
  • Did the candidate make arrangements for firm next steps to move the deal forward?

Do you think it’s a good idea to hire someone with exact industry experience, or do you see companies have more luck if they hire outside the box?

Ideally, you want that direct experience. If you’re hiring for a role that sells into IT, you should look for candidates who have experience selling into a technical team. If you’re hiring for a rep to sell into marketing, look for a candidate who has sold into marketing or sales, etc. Where thinking outside the box comes in handy is with the actual product the candidate is selling, which doesn’t need to be an exact match.

I would also focus on the transaction volume. If it will be a high transaction role, don’t hire a candidate who has built a career selling 1-2 large deals per year, and vice versa. If it’s a lower-level sales position, I’d be open to expanding target profile. At this level, individuals are not yet set in their ways and will be more coachable.

What are your thoughts about candidates coming from a large company interviewing at a startup or expansion-stage company?

If an individual has spent his/her entire career in large companies, it’s a hard no. But there are some caveats:

  • If a candidate worked for a smaller company that was acquired by a large company.
  • If a candidate has limited experience 1-3 years, provides the right reasons for wanting to make a move, and is working within a newer technology within a bigger company.
  • If a candidate has a mix of both large company and startup experience, and his/her motivations and expectations of working within an expansion-stage company are realistic.

Where have you seen good companies go wrong with sales hiring?

My top three mistakes to avoid are:

  1. Believing that candidates are only looking at your company. Top reps are constantly recruited, and just as a candidate is selling you on the reason they should be on your team, your should be selling the candidate on the opportunity. It’s a balancing act.
  2. Not having a sense-of-urgency in hiring. This can result in loss of momentum and loss of candidates.
  3. Not taking the employment brand seriously. It’s a small world in sales, especially within software sales if you are recruiting within certain markets. Just as you have a focus building and maintaining your brand within your customer segment, you should also be aware of your brand within the future hire segment. Take steps to improve and market your employment brand regularly.

Thanks to Carlie for sharing these great tips! If you have more questions about sales hiring best practices, please feel free to reach out to Carlie directly at [email protected].

Sample Questions and Free Sales Hiring Assessment

Download our free sales interview benchmark guide. Inside you’ll find the necessary questions to ask to really dig into a candidate’s experience and assess them on the three key components — Drive, Selling Skills, and Personal Attributes — that ultimately separate the best sales reps from the rest.




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