Wayne Lockwood: 11 Tips for Starting a New Sales Role

Author: Chris Gillespie

So you have a new sales job. The desk is clean, the laptop screen has shiny protective film, and your strategy is a blank slate. You feel giddy with excitement at what the future holds, and you can hear the cowbell clanging as other account executives ring in their deals. Quietly, you resolve to outsell them all.

But once you create your new Outlook signature (no .jpg images now, that’s a rookie mistake) and open a fresh spreadsheet, people begin joking “When’s that first deal coming in?” It’s then that you realize the pressure is most certifiably on.

Having been through this many times myself, I’ll share my top 11 tips for ramping quickly in a new sales role:

1. Leverage Your Mentor

Time is of the essence here, and while it’s going to take you months to truly soak up the culture yourself, you can speed up the process by shadowing your mentor. If you aren’t assigned one, approach someone who’s at the top of the sales leader board. Pitch them on how helping you will make them look good, especially when they help you sell something fast. Then, get their permission to spend time observing them in their prep, on their calls, and in meetings. You’ll soak up what to do and even more importantly, what not to do.

The bottom line: Get a mentor who’s invested in your success.

2. Learn the Tribal Stories

Stories are how you’ll learn why people actually buy from you. Case studies are a great place to start, but often, the best stories aren’t written down but rather passed from salesperson to salesperson in classic oral tradition. The ones that keep spreading do so because they contain invaluable kernels of wisdom.

For example, I recall a story about a salesperson who used to sell purely on talking–wouldn’t even share a presentation–and would pitch such a beautiful picture that prospects would buy sight-unseen. I don’t even know if this was ever true, but it convinced me to show less and talk more, and I can accredit more than a few deals to this strategy.

In my experience, no amount of videos, computer-based trainings, or datasheets will compare to listening to a seasoned salesperson spinning these yarns. In fact, after just a couple of months, even a junior salesperson can accumulate several years’ worth of sales knowledge through the power of stories.

The bottom line: Memorize as many stories as you can about why customers purchased from your company.

3. Learn How a Deal Gets Done

Leads morph into sales the same way a caterpillar does into a butterfly: they go through predictable stages. What are your company’s deal stages? Write them out. This includes learning who’s involved in each one, such as sales development reps, solutions consultants, sales operations teams, the deal desk, services team, legal team, etc. Know roughly what each group’s function is so that you know where to go when the time is needed. Use your newness as an excuse to bumble around, introduce yourself, and take people out to coffee.

The bottom line: Write out your company’s deal stages and who is involved at each one. It might look something like this: b2b deal stages

4. Know Your Numbers and What You Have to Do

It always amazes me how many salespeople don’t know or concentrate on their numbers. Without this focus, you’re like a kite in the wind, subject to every passing breeze. Your performance (read: income) will be just as unpredictable.

How many calls/touches do you have to make to start a conversation? How many conversations lead to a sale? Find the most metrics-driven person on the team and get some approximate conversion rates to start working with so that you have benchmarks for your activity.

For instance, if you know that you can close three deals each month, 35% of all open deals close in-month, and it takes 50 calls to start one deal, you should be making no less than 107 calls/touches per week.

The bottom line: Get a peer to help you fill this out:

($ average sale)(# of sales needed to hit quota) = (# of opportunities)( average close ratio of opportunities) = (# of conversations)(average conversion ratio of conversations) = (# of calls)(average conversion ratio of calls)

5. Identify Your Strengths and Weaknesses

To get anywhere in sales, you must play to your strengths without being crippled by your weaknesses. Find out what you are best at and where you need to improve. A simple exercise to figure this out is to list out all the activities that you do in your role and rank them in order of favorite to least favorite.

For me, that’s:

Planning
Virtual presentations
Mentoring
Discovery calls
Making slide decks
Negotiations
Cold calling

Done? Circle the bottom item on that list: that’s usually where you’re the weakest and need help. Hold yourself accountable for it and make your manager aware that this is an area that you want to grow in. Ask for their support and tackle it head-on by doing it repeatedly.

The bottom line: Make note of your strengths and weaknesses and always be improving.

6. Know What Is Expected of You

It’s critically important to set proper expectations so that you know how to exceed them. While everybody loves to hear warm, fuzzy, and optimistic things during the onboarding process like “With your experience, you’ll be performing in no time,” you need to iron out exactly what “performing” entails. Does that mean hitting quota in two weeks? Two months? A year?

If you don’t do this now, you could be blamed for, say, an unexpected team shortfall. Emotions always rise at the end of month and quarter, and this immunizes you from that. Save everyone the headache and create SMART goals (simple, measurable, actionable, realistic, and timely) and come up with exact numbers on what you will be expected to deliver and review it with your manager.

The bottom line: Get your manager’s expectations in writing.

7. Create a Plan That’s Actually Based on Reality

Management hired you and they’re excited about your potential—you plan to go in swinging and deliver your number faster than anyone else has before. But be extra careful about setting expectations too high.

I know plenty of sales reps that have optimistically forecasted doing 200% percent of their number in their first month because they were feeling good about it. Two months in, that was not the case. As you might expect, they’d fallen short and like Icarus, flew too close to the sun. Don’t put yourself in this position.

It’s far better to under-promise and over-deliver. These first few months are your chance to set a good and lasting impression with your boss, so aim to be the guy or gal who called 60% and delivered 80%, not the other way around.

The bottom line: Be realistic and create a plan that’ll allow you to over-deliver and post that goal on your desk.

8. Silo Your Activities for Efficiency

Trying to create lists, prospect, take notes, and strategize your next move all at the same time is a lot like trying to change gears on the freeway: you’ll create unnecessary friction and sparks will fly. That constant switching back and forth will wear out your transmission (brain).

So, break up different tasks like you’re on an assembly line and hit them one at a time: analyze your territory in one sitting. Come up with a list of companies and contacts in one sitting. Email through the list in one sitting. Call through the list in one sitting. Basically, do all your freeway driving one day and all your around-town errands the next. You’ll achieve a much higher top speed and get a whole lot more done with a lot less mental strain.

The bottom line: Tackle your activities one at a time.

9. Activity is Not Productivity

There is a powerful learning curve to getting started in sales. At first, you won’t know what’s productive and what isn’t. Instead of sweating it, think of yourself as a scientist in a lab trying different combinations of chemicals in order to make a serum. Every experiment gets you one step closer to the answer.

And like a scientist, don’t get emotionally attached to the outcomes. As Einstein said, “I have not failed. I’ve just found 10,000 ways that don’t work.” After a few weeks or months, you should start to narrow down your focus to just those subject lines, objection-responses, and activities that were promising and achieve a far greater efficiency at selling.

The bottom line: Stay open to change and keep trying new combinations until you find what works.

10. Lean on Your Resources to Do the Selling

In sales, your job is to develop new business. Note carefully that nobody said that you had to do it alone. Just like you lean on your mentor, lean on your resources like solutions consultants, your manager, and even your company’s executives to help get it done. They want you to close your first deal, and you get to watch them work their magic and soak it all up. Once you get that morale-boosting first sale under your belt, then you can start to take things into your own hands and run the next one.

The bottom line: Don’t fight alone—ask for help closing your first deal.

11. Pay It Forward

“When I am tempted to criticize I will bite my tongue; when I am moved to praise I will shout from the roofs” – Og Mandino.

Go ahead and buy a few bottles of wine now to keep in your desk drawer. Why? Because in a successful sales environment, wine bottles are the “thank you” currency. Hand them out when people help you with things, like your co-worker in legal who stayed late to help you close a deal.

And when you’ve finally gotten a grasp on things, share your knowledge just as freely. Extend a hand back down the ladder that you just climbed up and help others just as you were helped. This is your opportunity to create the virtuous helping culture that we all want to be a part of. Pay it forward.

Feeling better about being new to the role? Good. Now, it’s time to put these tips into action. Have your own to add? Share them in the comments below!