How To Build Startup Sales Management Resources From Within

Being a Head of Sales at a startup is tough. Bigger companies have the resources to have front-line managers and training managers – all the things a startup lacks in terms of time and money.

The challenge for a Head of Sales is being able to run an effective, productive sales team while at the same time carrying out other responsibilities, like closing deals and working with the executive team on the overall sales strategy

Successful Heads of Sales know how to create a self-management culture within their sales team. Below is an easy framework to create more sales management leverage within your team.

Examine how you’re allocating your time

Time is the most precious resource a startup has – you want to make sure you’re managing it well. Make a bullet list of everything you do. Look at your calendar over the past few weeks and write down how you’re spending all of your time. This list could include pipeline reviews, performance one-on-ones, training sessions, daily stand-ups or executive meetings.

Write down all these things you’re doing as a Head of Sales without any kind of judgment about what it is. You want to capture 100% of how you’re spending your time day-to-day.

Categorize your list

Take this entire list you’ve made and group it into 3 categories.

The first category is things you’re doing that can only be done by you. For example, a meeting with the executive team about revenue updates or running commissions for your reps. There’s no one else who can step in and do this for you – at least for the time being.

The second category is things that you’re doing that someone else on your sales team could be doing but requires a bit of training. This could be running a training session or a pipeline review.

The third category is things you’re doing that someone else can do for you immediately, no training needed. This could be listening to calls or running a roleplay.

Start delegating

You want to push down and delegate some of these responsibilities that your sales team can handle. In the bucketing system above, give people the easier stuff first – don’t start off by having your reps take over your entire training session, for example.

Take a look at your current team and identify the reps you think have an interest and an ability to handle additional responsibilities. If someone is already struggling hitting their quota, you may want to hold off giving them additional work. Figure out who would be interested and the best person to do each of these things. 

Start out by giving them small tasks to see how they handle the added responsibilities. If it goes well, you can eventually move on to the larger responsibilities like delegating pipeline reviews, training or onboarding new reps.  

Begin coaching

This is one of the hardest things to do, but you’ll have to force yourself to stop doing and start coaching. It’s always going to be faster and easier for you to do something than it is for the person you’re training. Work with this new person, coach them and mentor them to pick up that responsibility and to do it really well.

Continuously give them feedback and help them work towards how you would want them to carry the ball.

Give recognition

If things are going well, you can provide cash incentives in the form of a spiff or a bonus. You can also make it a part of the career track to management if you can’t provide direct cash incentives.

If things aren’t working out, dig deeper to find out why someone isn’t fulfilling their responsibility well. Typically, people fail for one of two reasons. One is that they just don’t have the skills or the knowledge to run the responsibility well. If that’s the case, give them more support or training – but not too much training. According to Andrew Fayad of eLearning Mind, “[…] overtraining can be detrimental to your salespeople’s natural talent, crush their confidence and push technique over ability.”

The other reason is that they don’t have the passion or interest in taking on the responsibility you gave them. If someone doesn’t really want to do sales training and you put them in that box, it’s a bad fit and you need to reassess who on your team wants to take this responsibility. If someone isn’t interested in doing a job, then they’re just going to hold you back. Your sales reps won’t be set up to succeed if they’re not doing something they are passionate about.

You may need to shuffle things around until everyone is happy and able to excel in their role.

This is a simple process for sales leaders to create more management leverage within their team. Absorbing responsibilities without delegating and developing others won’t scale. It’s also very important to do this because you’re creating meaningful career paths and providing personal development to your reps. It’s worth investing in management resources very early on, even if the pain point isn’t huge. It takes time to get the system working, so start early.

Jordan Wan

Founder & CEO of CloserIQ. Previously Sales Strategy & Management @ZocDoc, Head of Analytics @PayPerks and Trading Strategist @Bridgewater Associates. MIT Bachelor’s & Master’s in Computer Science. CFA Charterholder.