Advice from six CEOs on building a killer startup sales team

10 September 2015 Matt Owen

Every business needs a sales team that can set up the customer-shaped pins and knock them down.

At DueDil it’s no different. We’re busy expanding our own sales team (and if you’re interested, you should check out our careers page). But what does it take to build the perfect team, and what mistakes should you avoid?

I headed over to Quora to see what the entrepreneurs and CEOs there had to say on the subject, and I’ve gathered up the best answers here for you.

Jerry Crespi: CEO at Allied Business Systems

Jerry Crespi is CEO Allied Business Systems, LLC, a consumer lending financial software business based in NYC. He suggests that while cultural fit is important, it should take second place to actual selling experience and qualified skills:

The biggest mistake I see any company (especially startups) make when creating a sales team is that they hire on personality rather than on learned skills.  Selling is a skill that has steps and right and wrong ways to do things.  So even if the person in front of you is outgoing, friendly, and has a track record selling someone else’s products, it doesn’t mean that he or she will be able to sell your products.

Not unless they have gone through solid sales training and sales self management training (this is how a salesperson manages the contacts, the followups, the written and verbal communications, etc.)  Then they also must learn your products or services to know what they are talking about.

You can follow Jerry on Quora

Jason M. Lemkin, Partner at Storm Ventures


In a similar vein, Storm Ventures Partner Jason M. Lemkin advised against being too impressed by previous record unless it was directly applicable to your sector. Selling at a multinational can be a very different experience than selling at a startup or SME:

You shouldn’t hire because she worked at Salesforce /Box /DropBox /whatever. Hire because they can close. Not because they are one of 4,000 reps that sell a product with $6,000,000,000 in revenues, a proven brand, and huge infrastructure behind it.

In addition to being a partner at Storm ventures, Jason is also CEO/Co-founder at Echosign. You can follow his Twitter account.

Jeff Osborn, President of

Jeff echoed this advice. He felt it was important to realise that cultural fit may not be always be achievable, but that doesn’t mean you aren’t hiring the right person for the job.

An expensive fail I’ve seen time and again is hiring a head of sales who can’t or won’t  sell by him or her self. The first sales hire for a startup had better be able to bring in revenue very quickly alone. Unless you’re flush with cash, the best incremental hire is a working, selling sales manager/VP. The trick is to get someone willing to sell but experienced at adding a team when it comes to that. There’s a lot of art and science to it.

Jeff also advised thinking about future responsibilities when making initial hires

Look for experience in being the first sales person and in hiring a team from scratch. Tempting but unfortunate hires include people who got lucky selling at a booming company early and ride that name to more jobs without ever doing the hard work of prospecting, forecasting, and closing deals.

Jeff is CEO at He can also be found on Twitter @osborn_jeff

Wisnu Subekti, CEO of

Wisnu heads up online educational site Zenius. He suggests thinking beyond direct revenue. Sales is also a hugely valuable source of business and product intelligence:

I define startup as a company that is still looking for its business model. So, when we are talking about startups, I assume the product is not fully developed yet and getting feedback from sales team is very important to improve the product. If that is the case, then not involving at least one of the founders in the sales team is one of the biggest mistake a startup can make.

His/her objective is not just to sell the product, but also to get direct feedback from the customers about how he/she can make the product better.

You can catch up with Wisnu on Twitter

Auren Hoffman, CEO of LiveRamp

Auren also talked about personality, but rather than looking for ‘the right fit’, he felt that different value could be found from different types of salespeople, and underlined the need to recruit and assign them accordingly:

Too many people overvalue extroverts when it comes to sales.  The popular myth is that all great salespeople are extroverts. The reality: many of the very top salespeople are more introverted.

It takes a mix of personalities and skills to build a great team. Auren explains in more depth:

For products that are intricate, involved, and strategic, one needs a product-oriented salesperson. That person needs to be a product expert and often needs to be both very technically capable and be very good about understanding a customer’s business objectives.  The product oriented salesperson also needs to be very good about follow-up and mapping out an organisation.

In my experience, the vast majority of great product-oriented salespeople are not extroverts.  Many of them are not pure introverts either (they are often in the middle) … but they are not the type of people who “own a room” and usually not the type that are buying the round of drinks at the bar.

auren hoffman

If your product is more of a commodity, then it is much more important that you have a relationship salesperson This person is extremely good at quickly forming relationships and this is really important because in a commodity sale, the relationship IS the differentiator.  In my experience, the great relationship salesperson tends to be more extroverted.

So be honest with yourself as to which product you have and hire accordingly.

You can follow Auren on Twitter

Robert Maynard, Founder at

Robert is co-founder of identity theft protection company LifeLock and founder He focussed on team growth and promotion.

While excellence should always be rewarded, direct promotion may not be the best way to make the most of an employee. Instead, consider were their particular skillset will provide the most value for the company:

Probably the biggest mistake I’ve seen in sales teams is to make the top salesperson the manager of other salespeople.  When you do this, gross revenues will always dip, your best salesperson is probably not a great manager because the best salespeople are greedy, self-involved and hungry, including, or maybe because they are so greedy.  Now when they have to lead people and coach them to their own success, they will often see it as taking money out of their pockets.

You can follow Robert over on Quora

Key takeaways:

Although their personal experiences were different, several key points did emerge from everyone’s answers

1: Find people who are willing to get their hands dirty

If you have sales in your job title, then you need to be willing to roll your sleeves up and actually close deals in addition to managing the team.

2: Hire people who are able to get to grips with your product

And help define it. Sales is increasingly consultative, even in consumer sectors, so your team needs to be able to balance relationships with in-depth knowledge of your business.

3: Put people where they can do the most good.

Top sales people may not be the best at managing others, so consider how they can provide value and continue to excel.

4: Don’t always hire based on personality.

Look for a concrete skills and sales record. While cultural fit is important, it may be that the ‘sales culture’ differs from the existing company culture. Consider what matters most to your business, especially when you are in a high-growth period.