Written by Seth DeHart · First published on Point Nine Land on Medium, October 2021

One of the biggest differences between B2B SaaS startups that scale fast and those that fall short of their full potential is… their ability to hire and retain top sales talent. In the early days of a startup, the first few sales hires make an enormous impact on the growth rate of revenue and in turn the growth of the company. If you make a bad hire for your first or second sales person it will not only slow growth but can kill the company. But I’m not telling you anything you don’t already know, so let’s get to it.

In this post, I’ll outline the criteria I use for assessing sales reps. I’m fortunate in that I’ve spent half my sales career building and leading sales teams in the US and the other half building and leading sales teams in Europe and while there are many obvious cultural differences I still use the same criteria for hiring Account Executives in both markets. I’ll refer to “sales reps” as Account Executives as this is the most commonly used term for sales reps at high growth startups and the below criteria applies to all seniority levels.

I’d like to mention that while I think the risk goes down with each additional sales hire, I believe that the first sales hire is the most important and sets the tone for everything sales related going forward. I can’t emphasize enough that the first sales hire is very different from the 10th sales hire. The first “Sales Pioneer” should be entrepreneurial and be comfortable with being a “full cycle” sales rep where they can create their own leads (like an SDR), but also manage sales cycles and close deals AND all while building the sales playbooks. I mention this because while the below criteria applies to all Account Executives, extra scrutiny needs to be paid to the above on the first sales hire.

The 10 Interview Criteria I use to assess Account Executives:

Trust
Hustle
Intelligence
Operational Excellence
Sales Skills
Industry Experience
Startup Experience
Coachability and Self Awareness
Likeability
Culture Fit

OK before I go into a bit more depth on how I assess each of these categories it’s worth mentioning that some of the categories are hard if not impossible to assess if you haven’t either been in sales or if you haven’t previously hired sales roles. If you’re building a B2B SaaS startup that requires sales roles then you probably have people in your network (friends, advisors, investors, partners) who have hired sales reps before and they must help you. The biggest sales hire mistakes are made by founders who haven’t hired sales roles before and as I mentioned this can be catastrophic. Many of the companies I work with at Point Nine are good at hiring, but they still include me and other Point Nine team members in the hiring process to get more perspective and further reference points on early sales hires.

First up is Trust.

For me this is simple. If I don’t trust a sales applicant then we are done. All the rest is irrelevant and as I go through the various points of criteria below, I’m always looking to make sure that everything they are saying checks out. If something smells fishy I dig deeper and if it still doesn’t make sense then I’m a “hard no’’ on the candidate. I can’t risk hiring someone I don’t trust and while this goes for all roles at a company, it’s good to remind ourselves that salespeople are often good at telling stories… So I’m always extra scrutinous to dig one layer deeper to get to the truth to know for sure if I can trust the applicant.

Hustle is a close second.

Hustle and hard work is essential to be successful in sales and it is one of the few things we can actually control. This is a bit tougher to determine in an interview, but I look for indicators of grit and perseverance. I like to find things that would be impossible or at least very difficult to achieve without hard work. Rapid career progression is solid or a high level of athletic success are both good indicators. I’ll sometimes ask a candidate to discuss their work ethic and examples of hard work they’ve done. Difficult to achieve KPIs around aspects of previous work can be good indicators. Without hustle the following categories are irrelevant as Account Executives without a strong work ethic will fail at a startup. Find hard workers.

Intelligence is obviously important.

Intelligence may be less important as you make more Account Executive hires and the Sales Playbook/System becomes more refined and easier to follow, but I want to build a sales engine with smart Account Executives and buyers want to buy from smart people. I always feel weird trying to assess a candidate’s intelligence, but if you’re in the position to hire then you should probably be able to identify intelligence, so use your judgement. Just don’t hire someone “too smart” for their own good. Sales is about repetition and if an Account Executive gets bored easily and starts chasing shiny objects they will not produce revenue consistently so be cautious of the very, very smart candidates who may get bored, lose focus and get distracted easily. Find the right balance.

Sales Skills is an obvious criteria.

During the recruiting process, the candidate is trying to “sell” to you, the decision maker, on why you should hire them, while at the same time you are trying to assess their sales skills. This is much easier assessed by someone who has sold previously. Average Account Executives are good at saying what you want to hear, but the best candidates show their advanced skills by asking strong questions. The best candidates can get a job anywhere and they are qualifying you (just as they would qualify a prospect during the sales process) to identify whether they will be successful selling your product. I love candidates who grill me and if I can go deep into sales methodology and debate best practices with a candidate then they usually have strong sales skills.

I work with sales leaders who swear by the “sales case study’ during their interview process. While I haven’t done this extensively, I like it. They want a sales rep to “do a demo” with them to see if they have a sales method. They aren’t looking for product knowledge (as the applicant doesn’t know the product yet) but the setup, discovery, ability to listen and set next steps and then finally the candidates ability to take constructive feedback from the hiring manager after the case study is complete.

Also, in that regard, it’s worth mentioning a cultural difference between American Account Executive candidates and European Account Executives. American Account Executives are very good at saying the right things but that doesn’t mean they can actually sell. European Founders often are very impressed and even amazed at how smooth the sales candidates are in the US, and they often make mishires for their first US hire(s). There’s a calibration that needs to happen when shifting from EU candidates to US candidates and hiring managers need to be extra scrutinous when starting the interview process in the US. A sales guy I met early in my career said to me, “I’m very good at interviewing. If I was as good at my job as I was at interviewing then I wouldn’t get fired all the time.” Think about that guy when you interview US candidates ; )

Coachability and Self Awareness

These categories are often correlated and everyone has areas where they can improve. If a candidate doesn’t have self awareness it’s very hard for them to improve. This is where I love the above mentioned “sales case study.” Usually an interviewer can find an area where the candidate can improve and if the candidate becomes defensive they are probably not coachable. Sadly most of the Account Executives I’ve had to exit from the business were either uncoachable or lacked self awareness and didn’t know when they were exhibiting a behavior that was unacceptable. It’s much easier to build a high performing sales team around Account Executives that have self awareness and are coachable.

SaaS Sales Operational Excellence

Operational Excellence is an area where I’m deeply passionate. I reference this repeatedly in my writing and it’s absolutely critical that Account Executives can run a very disciplined process. While many skills are needed to “sell”, scaling a startup requires a well run system and the better each member of the team is at running the system the faster the entire system and team can scale. When assessing this criteria I want to know if and how the candidate thinks about the math of a sales engine, conversion rates and end to end sales funnel/pipeline management. This is extra critical for the early hires as they will be building the processes, but every great sales person I’ve met is trying to turn themselves into a half human, half machine fully optimized sales engine.

Industry Experience

Industry Experience is sometimes extremely important and sometimes less so. While experience in the industry you’re selling always helps with ramp time and is sometimes essential to connect with the buyer, often times it’s far less relevant and the industry can be taught quickly. It’s usually a tradeoff between industry knowledge and other areas like SaaS Sales experience. I get excited when I interview a candidate selling in the same industry as we’re selling into. If they can teach me about their approach to selling into the industry it’s usually a good sign (not to mention it’s a bonus to learn from candidates). I trust founders to decide whether the need for industry experience is necessary to sell their product.

Startup Experience

Startup Experience is very important in the early days of a startup. Many of the failed Account Executives I’ve seen have gone from a large company to a startup (the grass is always greener in startupland) and struggled without all the processes they were used to at a large company. Large company Account Executives often ask for “the documentation on how we do a certain process” and the joke is “here’s a blank piece of paper, you can make one.” Having worked at a public company early in my career, I know there are a lot of places to hide in large companies. Doing sales at a large company is like playing futbol/soccer, as its easier to blend in on a large team if you aren’t talented. Sales at a startup is singles tennis. If you are bad, everyone will see you. If you are great, everyone will see you. That exposure adds a lot of pressure at a startup. For candidates who have worked at a startup(s) this will be normal and for candidates who have only worked at large companies the startup pressure can be overwhelming.

Likeability is usually pretty important.

“People buy from people they like.” Do you like the candidate? Do you want them on your team? This is criteria comes down to personal preference and it’s probably less relevant to be objective in this category as you need to have confidence that the Account Executive will connect with the buyer. It sounds harsh, but Account Executives who aren’t likeable don’t last in sales.

Culture Fit is ultimately up to the founder.

This is pretty straightforward, but its worth mentioning that building a sales team doesn’t have to ruin company culture. I know many founders are nervous that building a sales team will erode their culture, but if you add good people then it can be net positive to company culture. There are many kind and thoughtful Account Executives who happen to be motivated by money. After a few good Account Executives are added to a product led company I often hear from founders that a new accountability is added to the business as a whole with the growth of the commercial team.

In conclusion.

You will need to make tradeoffs on the above. Rarely does any one candidate rate high in every category. I always like to identify the risk factors associated with the above categories for each candidate and often I’ll discuss these with the candidates. I want candidates who are hungry and I’m extremely transparent (sales people like transparency) and I want the candidate to understand the risks around what they are getting into. Expectation setting is critical to building trust and also allows me to have that final conversation around self awareness with the candidate and see if they are really ready for this mission critical sales role in the startup.

I hope you found this helpful. There are many ways to interview and hire and I’m always open to learning more and finding ways to improve my process.

Hiring your (first) Account Executives