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The startup economy, somewhat ironically, is pretty unforgiving when it comes to short tenures with candidates. In sales, this can be your fault for not producing the numbers or the firm’s (impeding your way to make those numbers) or a combination of both. The former is under your control. The latter is also under your control – well, at least partially – and your main way to influence that in your favor is to vet the firm BEFORE you join and to hold off from joining if you see major red flags. If you are using an external recruiter – use their knowledge of the firm and the players to enhance any insight you can garner through your own research. In fact, a good recruiter does their own vetting of the firm before they start working for them so make sure you ask your recruiter about their due diligence on the firm and why they chose to work for them. Ultimatley the decision is yours though, so here are some key factors to consider before you take the leap in sales with an earlier stage firm (don’t forget to read the big caveat below though!!!):

  1. Financial health.
    This is especially important in these days of tighter funding markets. Finding a profitable firm is rare in the startup space but next best is one that is cash flow positive. Most startups are cash flow negative and are there by definition if they have taken in venture funding recently. Do your due diligence here – Look at the last round that they raised and ask about their burn rate and when they expect to go cash flow positive or raise their next round. That gives you a clear idea as to how much time they have to prove their value and get to cash flow positive status or raise that next round. 
  2. Market health
    My friend Chris Brinkworth wrote an interesting post about his decision to join a new firm about a month back. Chris is an expert in the space he is in so he had a distinct advantage in being able to assess the market and the prospective firm’s relative strengths. You may not be an expert in the specific market you are looking at but seek market experts out amongst your connections and get their guidance on the space. 360 degree feedback will give you tremendous insight on the market you are looking at. 
  3. Company / Product health within the market.
    Do some heavy research on competitors and ask your connections to weigh in on their thoughts. How does the firm rank in the analyst reports – Forrester waves / Gartner Quadrants etc? Who has backed the competitors? Then make sure the product works well – insist on a demonstration and check on pre-sales engineering support resources and ask where the product roadmap is ultimately going – do they actually have a long term vision for their product that they are delivering against? You should also check out peer-review sites from actual users like ItcentrationstationCapterra or or on the support forums of the firm’s own support site. these sites show actual user experience with the product and can be very revealing on how your future customers will feel about the product experience that you sold them. 
  4. Culture and work environment. 
    The interview process should give you a good feel for the company and the culture. Glassdoor reviews can help although they tend to be a bit skewed towards overly positive insider reviews and bitter ex-workers so take each side with a pinch of salt. Check on tolerance of remote working BEFORE you join. Don’t assume it is ok to work from home 2 days a week. Go into any position with eyes wide open and as full information as you can get beforehand.
  5. Marketing support.
    How much field marketing, content marketing and BDR/SDR support are you going to get?  What is their quality of the lead flow like? What systems and processes does the firm have around it? If it is light, make sure you are prepared to do the digging for your own sales leads. 
  6. Your future Boss/ your future peers
    Make sure you fundamentally like and respect your boss. Are they fair and easy to work with? Do they have a track record of picking successful firms?  Do salespeople follow them from company to company? Do they have a history of people making money under them? Talk to people who have worked for them before. Talk to your future peers in sales and get the view from someone actually doing the job.
  7. Compensation plan.
    Ask to see the comp plan and read the detail around it. Ask tough questions around how salespeople have done relative to quota and from a W2 perspective. In many startups, theoretical OTE is emphasized without talking about achievability or how to over-achieve on it. Of course, if you join an earlier stage startup, you might be the guinea pig and there is no precedent set based on what previous people have achieved. That is the risk you take for going earlier so know what you are doing when you sign up. 
  8. Their hiring process
    Your experience during the hiring process is worth noting and often it reflects on the firm itself. Firms go through different waves of readiness to hire and the professionalism of their hiring process. Sometimes this is indicative of the wider way they do business so if it is disjointed, unprofessional and lacking in communication throughout, don’t be surprised later on if some of that spills over into your day-to-day work experience. 
  9. Their bargaining skills
    Beware of the immature negotiator. The first time you may see your firm in negotiation action might be around your comp. Here you need to be aware of companies paying you OVER market rate without leverage on your part. This is a major red flag. Read this blog post to see more on this subject, but generally speaking, this can be a micro-representation on the rationality of the firm in question and their overall approach to financial management. Interestingly, every time I have seen someone paid more than 30% over their market rate (for base salary) the firm has either gone under within 6 months or a new management team has come in and cleaned house.

Caveat! Before you go through that exhaustive list for every opportunity……..Read this:

Ultimately you have to rely heavily on your gut on all these items above and sometimes you need to just throw caution to the wind. These are startups after all and risk is a big part of what is involved in joining. There is definitely a balance – you can overthink things and there can be a tipping point in the interview process where you have asked too many questions.  Only you or your external recruiter can be the judge of that. You can also overthink things to paralysis so if that happens, read these tips on how to get past those issues.

You should still make sure you cover off as many of these items as possible up to that tipping point during the interview process. That way you can help avoid large regrets down the road.

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