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10 Things I Learned (So Far) Carrying A Bag

I read an interesting article today titled 9 Silly Mistakes that Marketers Make, #5 in particular caught my eye

#5. Telling salespeople how to sell.

Some marketers attempt to train salespeople to sell, based upon their experience in marketing. In fact, selling is like sex; you can’t possibly explain how to do it well unless you’ve been doing it for a while.

It struck home for me particularly because I have spent the last 3 years on and off  “selling”. Having spent 20+ years of my career developing strategies and executing tactically on various facets of product, corporate, partner marketing as well as product management, I felt the need to challenge myself in a new area. One in which “carrying a bag” would put me out of my comfort zone, and as a marketer make me face the harsh reality of sales.

Like many marketers, I’ve been guilty of sales commission check envy, believing that many sales people luck out and rely on a collective support system to close deals, and possess little or no detailed product knowledge. As I soon found out, those were minor misconceptions that actually detracted from the bigger picture of what it takes to be a great salesperson.

I entered my new challenge with confidence, believing that I knew our products as well as anyone, could stand toe-to-toe with CTOs when grilled technically, and could rely on my marketing spin and positioning to align our products to the challenges and solutions required by customers. I definitely had sales fantasys of large commission checks in my future. So how did I do? I give myself a C so far in selling but I feel that I have added some A’s to my marketing game now that I see both sides clearly.

My 10 top learnings (so far, with many more to come):

  1. Relationships Trump Technical Knowledge – The adage “People by from people they like”  comes to mind.
  2. Building Relationships Take Time and Energy – Dinners, smalltalk, drinks and golf games may seem like fun, but it takes a certain personality and in many cases high tolerance-level individuals to pull it off
  3. Poor Quality Or Weak Funnel of Leads Spells Doom – It’s impossible to turn sand into gold, and even harder to find your own opportunities
  4. They Love Me, They Love Me Not – I’ve lost track of the number of great 1st meetings and calls with prospects who are “definitely interested, let’s do a POC”. Only to never respond to a follow-up until 2 months later, then after the second call, never respond to a follow-up, until the 3rd call etc.
  5. End Of Quarter Has Never Come Faster – Those increments of 3 months are pressure packed with targets that mean so much to the organization and even more so when you have family depending on your variable paycheck
  6. There Are So Many Things Out Of Your Control – Customer internal politics, organizational realignment, varying stakeholders and let’s not forget competition!
  7. It’s Not Over, Even When You Win The Deal – Getting my first commitment from a customer buy was exciting, then came dealing with procurement, and then beyond that actually getting a PO to recognize revenue
  8. Hunters Have To Farm Too – In a small startup there is no such thing as selling and running. If you have any designs on getting add-on business OR having this key account as a reference, you have to track and manage the success of the implementation. And more relationship building
  9. Marketing Materials Everywhere. Except The One I Really Need – No shortage of corporate brochures, white papers or datasheets, except I need something that speaks directly to the customers unique pain and viewpoint (fortunately I was able to create my own as needed :-))
  10. That Press Release Is So Hard To Get – As Marketers, we say “just write it into the contract that they will do a press release”. The reality is that the person who approves the sale has no juristiction to approve a press release. Doesn’t matter what is written contractually. Like you’re going to sue your customer for that press release

Bottom line, I’m still learning and improving my skills at both ends of the sales and marketing spectrum. I’m pleased to say that I have a much higher respect for top sales talent and what it takes to earn that big commission check.



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