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Sales Coaching, Sustainable Growth, Training

Recruiting, onboarding, and developing sales skills

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


As with other aspects of sales, recruiting and onboarding are most efficient and successful when there is a process in place. When making a new sales hire, companies should look for candidates that possess qualities, principles, and skill sets that align with the company’s culture and growth phase.

Skills at Different Growth Phases

Each phase of company growth will require different skills from your team members. Many founders mistakenly believe that the sales team they rely on during the early stages of the company will be the same team they need when the company scales to billions of dollars in revenue. While a business will not necessarily need a different team at each growth phase, team members can and should grow their skills to support the changing needs of the business. Founders must consider how to recruit for the current growth phase while also looking ahead to the next phase, the future needs of the business, and the potential skills it will require.

Seek out the following high-level qualities and skills when recruiting candidates at each company growth phase:

  • Start Up: Reliable; proven record of performance; self-starter; sets the tone for the culture your company will establish; may dislike the process at first
  • Grow Up: Enjoys creating, documenting, and building the process; able to listen and learn from situations and experiences; enjoys working with small teams and learning from them
  • Scale Up: Team performer; enjoys executing the process; dependable during business hours (9AM-5PM); likely prefers executing an established process rather than creating one, and therefore may require a bit more hand-holding

Cultural fit is just as important as performance; these particular types of skills cannot be trained and/or would require too much time to instill in a candidate. Ask the following questions pertaining to cultural fit when meeting with potential candidates: 

  • Do they work hard? Do they have a track record of working hard?
  • Are they able to identify and solve a problem rather than simply pointing out problems to a manager?
  • Do they take notes? Note-taking is an indication that the candidate is trainable and has the ability to execute a process.
  • Do they clean up after themselves? This is an indication that the candidate is a team player.
  • Do they ask questions? Do they seem genuinely curious about your business? 
  • Do they have experience that relates to your product?
  • Can they communicate with you? For instance, when you walk to get a cup of coffee together, do they start the conversation or do you have to drive the communication?
  • Do they display high intellect? Do they seem to enjoy using it to solve problems?

How to Recruit

As you begin company recruiting efforts, your hiring team should develop four to seven different criteria (e.g., empathy, curiosity, sales skills, diligence) on which they will gauge all potential candidates. Ensure that the entire hiring team understands exactly what is meant by each criterion. After each interview loop, ask everyone to submit their feedback using an online form. Then, schedule a time for the hiring team to meet to discuss the candidate. (The order of this is important as it avoids groupthink). Even if the candidate appears to be a definite “yes” or “no” you should still meet and discuss why, as this discussion can lead to interesting learnings. Small items may emerge as trends across all interviews and lead to an adjustment of your criteria or interview process in the future.

Recruiting can be very disruptive to normal company flow. As a practicality, it will monopolize a lot of your company conference rooms in addition to your manpower. During a period of active hiring, consider setting aside an entire day strictly for recruiting. Here is what that recruiting process might look like:

  1. Block conference room(s) for the whole day. Make sure they are clean ahead of time (whiteboard, etc.). This is best done on a Thursday. The CEO/VP/founder should block the whole day for “email” so they can interview potential candidates right away.
  2. Notify the front desk/EA/shared space lobby that you will have several candidate guests, and provide their names. 
  3. Offers for each job requisition should be pre-approved internally, so that you simply need to add the candidate’s name to it.
  4. Schedule 30-minute interviews with each candidate, along with 30 minutes of overflow at the end of each one in case it runs long. Those who your team identifies as rock stars should meet with the CEO/VP/founder immediately after their interviews.
  5. Candidates approved by the CEO should be asked to perform a role-play task the next day (Friday) on-site if possible or online if they do not live in the area and/or travel plans do not permit. For the role-play, they can sell their own material or they can use your standard company deck. See Table A for several exercises you might ask candidates to perform during this interview.
  6. Ensure that one person on your staff coordinates the candidates and interview process in a master tracking sheet

Table A. Role-play exercises for candidate interviews according to sales role

Table A.  Role-play exercises for candidate interviews according to sales role

During periods when you are not focused on hiring, you may still meet people who are a good fit for a role at your company. (For instance, your barista, Uber driver, etc.) Always have recruiting business cards on hand to give out. Use your regular business card or consider printing a different version that says, “I think you would be a great fit, and we’re hiring!”

Recruiting Best Practices

The job of recruiting should not be done by one person alone. It helps to involve others, even those with less obvious roles, in order to gain different perspectives. For example, inform the front desk manager (regardless of whether they work for your company) that you will be interviewing candidates. Then ask them for feedback about how the candidate interacted with them. Were they polite, friendly, rude, dismissive, etc.? Never hire a candidate who is disrespectful or dismissive to anyone on the team, regardless of role or seniority. This is bad for company culture and it can easily be avoided.

In addition to listening to what candidates say, observe their behavior as well. The following are common ways to identify important behavioral traits:

  • Do they take notes? In the first interview, state the five key things you are looking for in this role. An hour later, in the second interview, ask the candidate to repeat those five things. If the candidate does not remember, consider whether he or she will remember to take notes of key criteria on customer calls.
  • Do they clean up after themselves? Offer water to the candidate. Upon leaving the room, notice if he or she cleans up after themselves. Many team cultures are based on the idea that “everyone does the dishes,” so figure out if the candidate would blend in with that environment.
  • Are they honest and sincere? Throughout the conversation, gauge the candidate’s level of interest. Do they seem truly curious and genuinely interested in your company and this role? Are they asking questions that are thoughtful and applicable? 

While none of these actions alone should disqualify a candidate, as a whole, they will provide valuable insight into a potential hire.

Table B. Recruiting methods by growth phase

Table B.  Recruiting methods by growth phase

Using Recruiters

Many companies are uncertain whether or not they should use a professional recruiter. The answer likely depends on the phase of growth your company is in. Early on, you should hire people you know, however, once you enter the Scale Up phase, you will need to adjust your strategy. See Tables B and C for recruiting methods that work best at different company growth phases and sizes, respectively.

Table C. Recruiting strategies by company size

Table C.  Recruiting strategies by company size

To begin using an external recruiter, invite the recruiter to your company so that you can explain your company culture and the type of candidates you are seeking. Ask questions about how they can help: what they can offer, possible results they can achieve, compensation levels they recommend, etc. A good recruiter can provide you with job descriptions, pay analysis, titles, and more. Remember that recruiters (especially sales recruiters) are primarily sources for candidates, not hiring companies. They cannot interview candidates for you, and the depth of their duties does not typically extend beyond finding you the right “type” of  candidate, usually based on a resume screen.

You should only consider paying a retainer to a recruiter for executive positions. This will likely not become an issue until your company has reached about 25 employees. Before that point, you should still be searching for candidates in your own network and through VCs.

Common Recruiting Pitfalls

Pitfall 1: Hiring only when you need someone. You may say “no” to a great candidate because you do not think your company needs them yet. In rapid growth mode, however, you can always find a place for great people. Is the candidate open to a more flexible role until the company is ready? If yes, then make the hire. 

Pitfall 2: Your recruiting process is built around the candidate. During the Scale Up phase, your company may be interviewing a lot of candidates and scheduling per their individual availability. This can cause massive disruption to your business because it leaves your team unable to find deep focus time to get work done. Instead, organize a recruiting day each week or month, as needed. Properly prepare the organization by following the steps described above – block a meeting room for the entire day, clean up the office to make a good impression, etc. If necessary, hire someone to manage the front desk for the day. To facilitate a more concentrated recruiting process and avoid further disruption, the following steps are useful:

  • Inform your recruiter of your plans, and ask for their help filling the calendar for your recruiting day. They will likely be interested in helping as this creates a very efficient way for them to find quality candidates.
  • Have the recruiter perform the initial screening calls with the candidates to ensure quality. Have your hiring manager perform 30-minute interviews on a Thursday (followed by 15 minutes of overflow time plus 15 minutes to reset). If a candidate appears qualified, walk them to the CEO/founder’s office for a 15-minute conversation. Ask any approved candidates to come in the next day (or schedule a meeting online) for a 60-minute group interview by the executive team. 
  • If the candidate is successful in the group interview, perform a back-channel check with a trusted person using shared contacts, and then make the offer on Friday afternoon.

Figure 1. Sample calendar of recruiting process for a company during Scale Up phase

Figure 1.  Sample calendar of recruiting process for a company during Scale Up phase

How to Onboard New Employees

Recruiting is perhaps the most difficult part of finding successful employees, but these new employees will still need guidance and training before they can start producing. You must have some kind of onboarding program, as new sales reps are not ready to begin making calls on their first day. While your company might not have time to run a full onboarding program for every new hire group, there are ways to make the process easier. 

Use the following guiding principles to help make onboarding more efficient and successful:

  • Onboarding will not be completed in the first one or two weeks because humans can only handle so much new information at once. Reinforce your training over time using different methods (classroom, hands-on, role-play, etc.).
  • Onboarding and training new team members should be the responsibility of the entire company. Be sure that your existing team knows that training new hires is a worthy investment of their time and energy. The better prepared your team is, the better and faster the new rep can start contributing.
  • It is crucial that new sales reps hear about the company strategy directly from the founder and the rest of company leadership. This sets the tone, clarifies the direction of company, and explains the “why” behind it. This is a message that should be delivered directly from the source rather than getting passed down through different employees.
  • When onboarding new sales reps, many companies make the mistake of not letting the rep get familiar with the product. (This is even more important if you sell a technical product.) A portion of each rep’s training should include time spent working with customer support. Some companies have a requirement that every employee must spend a few days per year performing customer support duties.
  • Create a “buddy system.” Pair every new hire with an existing employee that they can shadow and learn from.
  • Your company’s onboarding program should improve each time you perform it. Get feedback from your existing team and new hires about how the program went. Collect this feedback immediately after onboarding is completed as well as a few months later once the reps have settled into their positions. They will have great perspective and insight on how to improve the program. 

Table C is a sample onboarding program to use for the first reps that you add to your team.

Table C. Sample four-week enablement plan for a startup (e.g. the first rep)

Table C.  Sample four-week enablement plan for a startup (e.g. the first rep)

Record everything you can. The easiest way for a sales rep to learn is by watching and reviewing their own work.

As your company moves into the Grow Up and Scale Up phases, your onboarding needs will become very different from the Start Up phase. See Table D for a more extensive sample onboarding plan to use in these later stages of growth. With a variety of speakers and modes of learning, the entire company should be helping to train new hires.

Table D. A four-week enablement plan for onboarding new reps in Grow Up and Scale Up

Table D.  A four-week enablement plan for onboarding new reps in Grow Up and Scale Up

Training Specific Principles and Skills

Regardless of role or skill level, there are a few core customer-centric principles that everyone on your team should embody and regularly rely upon during the sales process. See Table E for five key selling principles that should guide your team. 

In addition to those fundamental, customer-centric principles, there are several core skills that each person in each role must have. See Table F for a breakdown of the basic skills necessary for each particular sales role. (Note that the Sales Director should have all of these skills but focus on the ones indicated.) Figure 2 displays how and when each role comes into play during the sales cycle in the early phases of company growth.

Table E. Customer-centric selling principles

Table E. Customer-centric selling principles

Table F. Core skills to master for each sales role.

Table F.  Core skills to master for each sales role. 

Figure 2. The key sales roles across the sales cycle

Figure 2. The key sales roles across the sales cycle

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