The first of first days as the boss

This is the first of several posts on my first opportunity as a true leader focused on sales training. From the three reps I acquired to the team of 60 I mentored, the drama unfolded for the betterment of myself and all those paying attention.

Sales training is an art form and here hopefully this story will share how I became a star…

I walked through the door, hungry and full of two monumental feelings. The first, that I deserved this opportunity and it was about time it presented itself. The second was THAT I HAD NO IDEA WHAT I WAS DOING and was going to be exposed as a fraud quickly. Up I went, following Paul up the thirty something stairs in flickering dim light, into the broken down law offices that were now the headquarters of JobRanch. There was fake wood paneling on the lower half of every white paperboard wall. The panels split into empty wall-fixed bookshelves where tome after tome relating to the history of cases used to reside. There was a stale smell in the air, and as we turned and entered the CEO’s office my heart raced with anticipation.

I got this job for three reasons:

1. Paul, my boss, hired me while he was VP of Sales at SurfControl. I joined as a member of his sales team. I actually reported to one of the managers below him, and quickly gained the respect of the organization. He left to start JobRanch, and as soon as he could afford to, he proposed that I join the team. I debated making this move. While I was bored with the day to day at SurfControl, it was easy for me to maintain a position at the top of the stack rank. By making this leap into the Startup world, I was putting my career and my family’s security at risk.

2. My ability to communicate the particulars of my sales success was apparent to the CEO Dave, and we clicked right away. I would not say that Dave was the best hiring manager out there; his gut instincts about people are hit or miss. In my case he made a good read, and while he had some valid reservations, he decided to give me a chance.

3. I was willing to take on the role of Director of Sales for cheap! They were paying me less than I was bringing in as a rep, but oooh, my first batch of stock options. Do not let the options fool ya, get the money, get the money.

Dave was sitting at his desk while Paul with his $100k smile and I with my inexhaustible desire stormed into the room. They seemed glad to have me and show me around. He brought me to my office, a tiny windowless box at the end of the hall. It was 7 am in February, and already the room was starting to cook. I threw down my briefcase on my new rickety wooden desk. I noticed a stale scent of mildew in the thick air.

Paul walked me through the sales floor, a big room with desks and no cubicles, telephone and internet cables taped to the walls and floors. He introduced me to the three salespeople, a man, 40 going on another shot of whiskey, another gentlemen, 25 and on parole, and an Indian woman, who was days from going home to Maharashtra. The dysfunction was oozing from the walls, and if I knew then what I do now, I would have dropped my briefcase and bolted out the door, or perhaps the second story window. But in that moment, I can recall the sense of adventure, the sense of challenge and excitement. I felt that I was right where I was supposed to be, and while I did not know it yet, a Startup Sales Mentor was born.

We talked for hours that day, Dave, Paul and I, and by lunch more and more ideas were flowing as to how to build this sales organization. A few things were abundantly clear:

1. Since we were offering a free trial, communication with large numbers of organizations was vital.

2. Success in our Baltimore site was because of the quality of product. Job seekers were flooding to the site.

3. There was too much territory and work to be done to not segregate responsibilities into lead generation and sales roles.

4. The process and workflow had to be scrutinized and then re-tooled for efficiency.

I remember driving home with Paul that afternoon and idea after idea as to how to make this work continued to leap from our mouths. The executive team seemed strong and while I would learn that there was folly in that assumption, for the moment I was in heaven.