My first impression of world of enterprise sales was that it was a job for lone wolves. They generally did not hangout together other than at company outings like sales kickoffs and presidents club trips. They were not very willing to share what they did to be successful. Sales managers often had little control or sway with the reps and salespeople did whatever they wanted.
When I entered into sales, it was an accident. My career journey started through programming. I had taken a move to San Francisco to be a consultant and help the sales team on occasion as we rebuilt our West Coast territory. Within 3 months, there were no sales reps, and I was asked to carry a bag.
Unlike today, there were no online resources like blogs, videos and podcasts. I am talking before Google was a thing and when most companies still did not have email setup for employees. There were books, but trying to find classes or sales coaches or mentors was not easy. Even when you found a coach, how could you trust what they were sharing was even useful?
I was thirsty for knowledge. It made no sense that everyone should go through the same struggles as a new rep. So I sought resources and people that could help me avoid rookie mistakes and accelerate my learning. I read a few books like SPIN Selling (a classic and still relevant). I pinged my boss relentlessly. I gravitated toward any resource I could.
There were events for salespeople, some of which I attended. Most of these gatherings however were more networking events geared to people selling to each other. Rather than trying to help each other, it was more “what can you do for me.” As a new rep, I had nothing to offer and made no connections.
When I joined Siebel a few years later, it was the first truly professional enterprise sales organization I encountered. These were true masters of the art that sold the big deals, built executive level relationships and exuded confidence. I could observe what worked and did not work. Some of the reps were kind enough to give me some pointers. I had the benefit of a tight-knit and supportive team in New York. It was the first time that I felt that I belonged in sales and could be successful. Though the road was hard and paved with plenty of potholes, it is a road that I traveled on to success.
Fast forward two decades and I still see many salespeople struggling. The statistics on quota attainment, rep longevity and sales productivity have not moved appreciably. Salespeople and managers are still making the same errors. Instead of moving the needle on sales excellence, we are mired in the pit of sales mediocrity.
There is no logical reason for the sales profession to have not significantly improved in this time. We have a trove of quality resources on the Internet. The number of books and blogs and videos and podcasts has exploded over the past several years. You can find numerous training and coaching resources, all simply a click away. There are plenty of seminars and workshops and classes to avail oneself of. And if you want to find other salespeople to connect to, LinkedIn gives you access to thousands and millions of possible connections.
Yet, a career in sales is still very much a lonely profession. The era of the lone wolf sales rep may be on the way out, but many sales professionals, especially the millennial generation, feel they have no one to turn to. There is no safe place to ask the rookie questions or to seek unfiltered advice or to admit failure. Many of us may be on sales “teams,” but you might as well be by yourself.
One of the most admirable traits of the tech industry is the desire to come together and help each other out. There is no sense of dog-eat-dog competitiveness or the need to keep secrets. The open source movement is one outcropping of that spirit of community and shared purpose. Sure, there may be some ribbing of the “noobs,” but those “noobs” have a community that they can be accepted into, learn from, find mentors and thrive in their chosen profession.
The tide is turning in sales. No longer does it make sense to leave sales reps to sink or swim. It is too expensive hire reps and let them “figure it out,” only to churn them out of the job. Sales is too important and the risk to revenue too great. While we have optimized technology and processes, our approach to talent and culture building is still in the dark ages.
What if instead we treated sales as a community? Just as they have communities for programmers and startup founders, sales also needs community — a community that comes together in person. Online channels are helpful, but no one learns simply by exchanging messages on Slack. We learn when we can have a conversation, when we can hear for ourselves the good and bad, and then probe deeper and exchange ideas. That 2-way conversation is about helping each other as opposed to approaching it from the attitude of “how does this help me.”
Community is also about the tribes we form in our own companies. Competition is natural in sales, but so is cooperation. The competitor is not the person at the desk next to yours, rather the competition is all the options customers have to avail themselves of beside your solution. That means rethinking compensation plans and contests to be more team-based. That means fostering more peer initiated learning opportunities. That means building more cross-functional teams between sales, marketing, product and engineering to work on deals together. Lastly, that means taking the radical approach celebrating the team over the hero rep.
Why am I so high on sales communities? Because I have seen them work, especially when it is done in a grassroots, non-commercial way that emphasizes the value to salespeople. More importantly though, the speed of change in the sales industry is forcing sales reps to be better and adapt to change faster. The era of relationship selling is over, and sales reps are expected to be more than just purveyors of product information. They need to be equipped with the skills and motivation to succeed.
One time I was chatting with someone at an event and they shared that what they most valued was that they did not feel alone. Working in sales is a tough, one of the toughest professions mentally because of all the rejection one faces. She felt that she was supported though because she had a community to share with and learn from and ask the questions she did not feel safe to ask of her manager.
In the past year of building the Enterprise Sales Meetup across multiple cities, I have seen the power that comes in building communities. People are building their professional networks, sharing ideas and learning about work in sales. It is a place people can come with their questions and not feel judged. Each person comes away with new connections, practical tips and the inspiration to achieve.
If you manage a sales team, I encourage you to think about the power of communities in fostering greater teamwork. Ask yourself whether you have a team or a group of lone wolves? Do your sales incentives encourage collaboration across the team? Are sales reps empowered to freely help each other? Do you offer opportunities to help reps and other managers to connect with professionals, build their networks and expand their learning?
If you are a sales rep, you should consider how connecting with a local sales community can expand your horizons. Networking is a force multiplier in accelerating your career trajectory and success. Not only our are you building relationships that can yield opportunities down the road, you are also learning and sharing with others, increasing your knowledge, credibility and professional standing.
This article was originally published on Strong Opinions, a blog by Birch Ventures for the NYC tech startup community.
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