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PDF Editor FAQ

Jason Lemkin stresses out the importance of hiring great VP of Sales (when the time is right). What is the path to become a great VP of Sales?

Each story is different, but there is one clear penultimate step: recruiting and managing a small team yourself.What 95 times out of 100 is a recipe for failure is jumping straight from successful individual rep to VP of sales. If you are the #1 rep at a hot startup, you will get VP of Sales offers from other up-and-coming startups. A CEO or two will want to take that risk, to hire the #1 rep at Hot Startup to be their VP of Sales. My advice is don’t take that job.Instead, you have to learn to recruit. 50% of the job of a VP of Sales is recruiting a great team. Not just managing one.A related mistake is a director of sales who inherited a team but didn’t recruit one, jumps to VP of Sales. That almost always = failure as well.Take your time, get promoted at least to manager or director level and recruit 2–3 reps yourself that hit quota.If you can find a way to recruit 2–3 that can hit quota … which is hard, and a very different skill than hitting your own quota … you can recruit 20–30, or more.You then can be a very successful VP of Sales.

Is Salesforce good for startups?

The one thing I do strongly recommend is letting each VP you hire pick her core tools and system of record.Forcing a VP of Sales to use a CRM she hasn’t used before or isn’t comfortable with is a huge tax on her time. Don’t do it. Same with your VP of Marketing and your Marketing Automation system, etc. If you like Hubspot but your VP of Marketing likes Marketo … go with Marketo.Given Salesforce’s overwhelming market share in tech companies in particular, your VP of Sales, once you hire her or him, is likely going to want to use Salesforce.So at least plan on using Salesforce once you hire your VP of Sales.Forcing a VP of Sales to use a CRM she isn’t comfortable with is a significant drag on productivity — and thus, sales. Don’t do this.Should you use Salesforce before then? Well, that depends on what’s easiest on you while you are interim VP of Sales. If you haven’t used a CRM before, use something like Pipedrive. Pipedrive is basically Trello for Sales. You can figure it out in about 5 minutes and it is very elegant software. It’s what you probably think CRM is/should be, if you haven’t used a CRM before.If you’ve used Salesforce before, or want to, well it’s overkill for between 0 and 2 sales reps. But if you’re going to end up there anyway, it may be worth using it early. But again, while you are the VP of Sales — pick what’s best for you.Just be ready to change when you hire your VP of Sales, that’s all.

What is a typical organizational structure for a SaaS startup with sales reps?

A rough structure for your first 1–25 sales reps:Early days:CEO acts as VP of Sales.CEO hires 2 reps, in the beginning, each barely pays for themselves, but by months 4–6 they are able to close 3x-5x their total compensation.Once 2+ reps can do 3x-5x their comp, the model gets pretty efficient.Then:Have to scale from reps 3–8 or so. CEO often struggles to manage so many directly.CEO starts looking for true VP of Sales before $1m, ideally hires one by $1m in ARR.VP of Sales hires next 5–10 reps herself.After 8–10 reps, you have to add more management:A VP of Sales can probably only manage 6–8 reps and a handful of SDRs herself.So for each 8 AEs or so, and 8–10 SDRs, you need a Director of Sales.You also start specializing more here. Segmenting by customer size, and sometimes geography.By 15 sales reps, you probably need a first head of sales operations to handle training, onboarding, compensation, quotas, etc. Earlier if you can afford it.

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