Lean on... Who?

By Teddy Chestnut

A lot of obstacles can get in the way of accelerating your career at a big company.  Top-heavy hierarchies can clog openings and extend promotion timelines.  Bureaucratic and standardized assessment processes can cap your career’s speed limit.  Slower growth creates less opportunity.  The list goes on.  (Of course, this is why it’s more fun working in a start-up…)

But large companies do provide at least one incredibly important asset to help high potential employees step up their game: a broad support network.  When you’re promoted to the next big job in a big company, there is always a group of people who have made that same transition.  They know the challenges you’re likely to face, the mistakes they have made along the way, the things they would have done differently.  And they are on your team.  They’re right around the corner, they work in the same office.  The best big companies spend a lot of time and money building the support networks that keep rising stars afloat when they jump into the deep end.

So what happens when you join a start-up as a sales associate, and nine months later you’re promoted to sales manager?  And then nine months later you’re a director, and a year later you’re VP of sales and service?  What do you do when you wake up and realize that there are 100 people reporting to you – you, who a few years ago had never managed a single person, and didn’t even have any expertise in sales to begin with?  How do you learn to transition from being good at selling to being good at managing a team, structuring a pipeline, developing a sales dashboard with the right metrics, and setting sales strategy?  Who do you turn to when you’re staring down challenges that you’ve never faced before?

You might turn to your CEO, but she invariably has a lot on her mind, and moreover, she probably doesn’t know what it’s like to be the head of sales.  She might provide moral support, but you need more than encouragement.  You need someone with perspective, experience, and an understanding of what you’re going through.

I had a great conversation this week about this very question with Mark, the head of sales for a Boston-based start-up that has grown exponentially in the past few years, raising $100 million in capital and reaching $60+ million in revenue.  Along with the company, his career trajectory has been meteoric, thrusting him into a new and bigger role at least once a year.  This was his advice about how to manage the challenge of blazing a career path when you don't have anyone in your organization to lean on:

1) Learn from your industry peers.  When he took the VP of Sales role, Mark immediately set up informal conversations – over lunch, coffee, beers – with 20 other local VP’s of Sales.  He picked their brains about how they ran their organizations, asked for their advice, and shared some of his challenges.  Surprisingly, many were more than willing to help, and while not every conversation yielded a gem of advice, some did.

2) Find a personal mentor.  Having someone you can rely on – someone who knows you and will work with you over the long run – is an essential part of learning.  Mark described that he found a mentor through his network, and that one of the most important characteristics of their relationship was that his mentor was always willing to challenge him.

3) Establish up a formal, external support group that meets regularly.  Mark formed a group of sales executives in Boston that meets informally over dinner once a quarter.  There are about 12 individuals in the group – maybe 8-9 show up for any given dinner – and they were all handpicked for their relevant expertise.  At every dinner they go around the table and give a short description of a challenge they’re facing – and then they go around again, offering advice.  Topics have ranged from the professional to the personal – the bonds between these executives have grown strong over time.  Some have even decided to work together. 

Stars at start-ups often have to navigate through uncharted waters – for their companies as well as themselves.  Going it alone can be a tough experience.  Instead, do as Mark did – reach beyond the walls of your organization to build support networks.  Your peers are likely to be receptive: they probably need someone to lean on as well.


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