Don’t want to start from ground zero? Hiring a seasoned professional has its advantages. 

In a previous post, I talked about the importance of getting your sales and product strategy in order, before jumping into your first sales hire. For someone like me, while daunting, this task doesn't feel insurmountable: I've been a sales rep, a sales engineer, and a sales leader. I know how to do early sales exploration, work out what my product fit is, how to build my buyer personas, who to approach for feedback, and then how to do A/B testing, till I have an approach that works. 

I know how to do all this because I've done it before, at other companies, with some great bosses mentoring and steering me into greater productivity and effectiveness. I've had a career in sales, before ever stepping into entrepreneurship. 

Could I do this if I hadn't had all that experience? Yes, I'd like to think so. But I know for a fact that I wouldn't have done it well, and I would've made a LOT of mistakes. Mistakes, as we solopreneurs are keenly aware, can hurt us. 

Would I recommend that a solopreneur friend with no sales experience whatsoever take on building his own sales strategy and bring on inexperienced sales reps that he can then groom into super sellers? In one word: no. It would feel irresponsible. I would, instead, recommend that they bring in someone that is either a sales leader, or has a potential to be. 

Hiring a Sales Leader as your first hire 

Scary? Yes. When you need to scale your efforts quickly, this is a very risky, and very scary next step because this critical hire can make or break an early stage company. This isn't hyperbole. 

In the early days, your sales leader needs to have several skills to help your startup scale. You need someone who can roll up their sleeves and get their hands dirty. They need to pick up the phone, cold call, write scripts, and everything else that goes into managing a sales cycle end-to-end. This, without your constant supervision. 

More importantly, this person also needs to be comfortable with risk, and with a lack of structure. Your company is still evolving, after all. They need to understand that they will continuously need to improve the strategy and pitch, and that they serve as the foundation for the feedback loop between sales and product. 

There are a number of ways you can go about sourcing this person. But if you're hiring someone full time…  

You're unlikely to find this person at a blue chip company 

That's an obvious one. Sales leaders, who have grown in their roles in large corporations, are too comfortable. They aren't likely to have the hunger, or the comfort with discomfort required from an early startup sales leader.

The best place to find them is at another startup. Look for people who have risen to leadership roles in other startups, and who want to use their skill set to build another early stage company. What you're looking for is a leader who doesn't mind jumping back into the role of an individual contributor. 

The next best option are folks recently promoted to management. These folks know they have a long road of middle management ahead of them. They also know how to do the work, as an individual contributor, and they have *some* experience managing reps. They'll hit the ground running and immediately impact revenue. The only flipside here is that they will expect to be head of sales down the line, so manage expectations early. 

Another option is a sales rep with a strong sales record at a startup, with no sales management experience. This is not a great option, but it is a good one. This person will be a self starter, need very little hand holding from you, and will probably do a pretty good job of creating a sales strategy that works for them personally, which you can then riff off of. The downside is that they'll need a lot of guidance when the team grows, and they have to switch gears from individual performance to group performance. 

However, if you're struggling to find the right candidate, or if you just can't afford it… 

Hire experienced sales reps 

Don't just hire one. Hire two. It feels counterintuitive, but it makes a lot of sense. (To save time screening the right profiles for interviews, try skill assessments on Equip!)

Nothing beats a sales rep from another startup. They understand the pace, they understand the lack of structure, and they understand the importance of stellar performance (and the opportunities that that unlocks in startups). Reach out through your startup network - every middle stage and late stage startup has high performers who are hungry for growth, but have nowhere to go in their current organization. 

In a pinch, a senior sales rep without startup experience will also do, provided they don't only have experience of working for large companies. Be wary of people who boast of their rolodex (connections/clients/prospect lists) because you'll need someone who can cold call when their rolodex is exhausted. Your startup needs to scale at a blistering pace, something your sales rep needs to understand. 

Your first reps don’t need to be A-star sellers, but they should be experienced in the art of selling and have a good understanding of the sales process. Four to five years’ worth of experience is ideal.

You may be tempted to go for inexperienced sales reps, and yes, this is the less expensive route. If you don’t possess a vast knowledge of sales yourself, however, it’s best to avoid it. Remember, we don't just get better at things with practice! We need mentoring, training, someone who can help course correct, and model best practices. But if you aren't equipped to do that for your sales reps, you're not doing yourself, your startup and them any favors. Having said that, this approach works pretty well for those entrepreneurs who come from sales themselves

Protect your company culture 

No one enjoys firing an employee. But, as a startup, you need to be fierce about protecting your culture. A startup that doesn't believe in itself, that isn't scrappy, isn't going anywhere fast. By holding on to poor performers, you're being unfair to the rest of the team. Pretty soon, they're performing poorly too, and company culture has shifted in a negative way. Before you know it, you aren't needing to fire one bad performer, but the whole lot and start anew. All of which could have been avoided if that first poor performer had been cut. 

As with everything else, you need to allow yourself to make mistakes when it comes to people too. It's impossible to only pick the good hire, to spot every lie on a resume, to build an ace sales team without hiccups, to nail every product demo and every cold call and every deal. We're going to make mistakes, and they'll hurt us. They'll also teach us. 


You wouldn't be here, reading this, if you didn't already have a pretty good appetite for risk, and the nerves of steel one needs to start and scale their own business. So, if your business is ready, take a deep breath, and take the plunge.