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19 Candid and Honest Insights from a Director of Sales at an Enterprise SaaS Company

An Enterprise Sales Director shares her candid, honest insights on career advancement, role and compensation, and the sales process.
Honest insights enterprise sales director

Recently there was a very candid AMA (Ask Me Anything — a digital version of a Q & A session) on Reddit from an Indiana-based Director of Sales at an Enterprise SaaS company. The post is packed with great insights for sellers at all career stages. Topics include details about her current role, career advancement, and her personal experience as both an individual contributor and sales manager/leader.

The full AMA is definitely worth a read. We picked out what we thought were the most valuable points, cleaned up the writing, and added a little context to make for some easy reading. Check it out:

Career Advice

What advice would you give to a top performer who wants to move into a sales management or leadership role?
Treat it like you would a sale. Find out the internal objections that exist and work to overcome them. Always be direct. Tell your manager that you are limited in your current position and that there isn’t much room for growth.


For enterprise sales positions, would you considering hiring someone who works in SaaS sales already and consistently reaches 150% quota attainment, but has a much lower average contract value and sells to SMBs?
I would definitely look at a resume with this type of experience.

Can you take us through your career path timeline? A director of sales is a position I strive to attain in the future, and I would love to hear your word of advice on your transition from rep to management to director.
The best advice I can give is to communicate your path to those around you. I was direct with my bosses once I realized I wanted to get into sales. I was very clear with sales leadership, all the way up to the Chief Sales Officer.

People didn’t take me seriously at first, but I continued to execute and over deliver on my projects, so they started to pay attention. When they moved me to sales, they thought I would fail. And I did fail. My first year I hit 30% of quota. My second year I hit 60%. My third I hit 100%, and I’ve been at 100%+ ever since.

When it came to management, I did the same thing. I went out of my way to help new reps and be a team player. During that time I communicated to everyone, that “I want to move up.” It took me a couple of years, but that’s how I got to where I am today.

What are the best tips and advice you have for people that are just starting their sales career?
When I first started, I thought if I worked harder than anyone else, I would succeed and be the best. I burned myself out and didn’t sell. I learned that I needed to work smart, not hard: I needed to manage my time better, and focus my team on the actives that delivered the most value. Take advantage of the resources provided by corporate, sales engineers, demo leads etc. Also, it’s imperative to realize early on that there are two processes you must master 1) a sales process, and 2) a close process. Everyone sees the sales process and thinks it’s easy. No one sees the close process. It is the hardest part of earning the sale.

I work at a mid-sized software company doing mid-market sales. I recently graduated college and started this job the same month. I trained for 2.5 months and have been selling since November. I beat Q4 2015 and have beaten Q1 2016 numbers already. My OTE is 50k. Our sales cycle is long and our price tag is low. Do you think it would be a good idea to try and move to another company where the path would lead to enterprise sales, but start there as a BDR and work my way up? Or should I stick it out here, deal with the low pay, but get more actual ‘selling’ experience, but have no chance of moving up to an enterprise sales role?
If you can stick out, outside sales experience is better for me when I’m reviewing a resume, you won’t get that with a BDR role. Also, I would stay in B2B software if you can. That’s the first thing I’m going to look for on a resume.

What do you look for in applicants that are fresh out of college?
I specifically look for people that are aggressive and hungry. We want sellers that are looking to take the next step in their career that we won’t have to babysit. I also look for candidates that either have a background with our industry/product or sales experience.

I work in marketing but loathe not getting paid on commission and I love the fast-paced nature of sales. How do I get into sales while not going straight into a BDR role, or taking a huge pay cut?
Find a sponsor within the sales team, preferably someone you would likely report to. Be clear in your communication that you would like to transition to sales.

What do your top rep’s do differently than the rest?
They have a weekly routine that they stick to. They have a sales process that they stick to. It’s not very complicated, but it requires discipline.

Role and Pay


What’s your OTE?
My on target earnings are $366,000 a year.

What is your commission compensation structure for you and your reps?
We pay 5-15% on gross profit of the the total value of the contract. Reps are paid 50% on contract, 50% on first bill paid in full. I’m paid 2% on the gross profit of all contracts and I’m paid 30 days after contract signature.

How much time do you spend working on forecasting or coaching reps?
50% putting out fires, 40% coaching, 10% forecasting.

What deal are you most proud of?
When I was a a rep I closed a $1.1M deal at 7PM on New Year’s Eve.

Sales Process


How do you get large businesses interested in your software when cold calling?
With phone scripts, I’ve always taken an “assumptive” approach. Rather than asking, “Are you in the market?”, I tell them, “I’ve heard you are in the market.” For those that aren’t you look stupid, for those that are, you’ve already shown some value. I look at sales as a game of statistics. I have to make 100 phone calls to find 1 project. I have to find 100 projects to find 1 project that’s ready to buy today. If you regularly and consistently put the work in, you will be successful.

How do you qualify leads over the phone?
We use the BANT approach (Budget, Authority, Needs, and Timeline). If we cannot verify those attributes, we do not consider it a lead.

How do you remain positive when things aren’t going your way?
This really comes with time. After you’ve been doing this for a few years, you learn to handle the peaks and valleys.

As a director of sales, how involved are you in actual sales?
Most everyone on the team is self-sufficient, so I spend a lot of time putting out internal fires caused by corporate bureaucracy, or putting out external fires created by prospects with unique requirements.

Do you offer any offer any discounts on your product?
We offer discounts on setup fees, but not on monthly billing.

Where would you find a list of medium sized businesses to sell to (or large IT departments)?
I am a religious user of Data.com