The Sales Coach: Gabrielle Blackwell

Welcome to the sixth installment in our  Sales Coach series. This month we’re featuring Gabrielle Blackwell, a sales leader and problem-solver with an appetite for changing the status quo. Gabrielle is a Business Development Manager at Cloudability, focusing on taking concept to action and idea to market.

Click the video below to hear a bit about what Gabrielle is going to share in today’s interview.


Tell me about your journey into sales.

I stumbled into it. I took the job out of desperation. After graduating from the University of Chicago, I thought about going to law school but I was burnt out on learning in an institutional setting.

I went abroad for a couple of years, and when I came back, the companies I wanted to work for told me I was overqualified for the new hire programs, but I didn’t have enough experience to come in as an experienced hire. I had to pivot my entire job search. I applied to my first sales development rep job at Cloudworks on a Wednesday, started on the following Wednesday, and never looked back.


Looking at your resume, you seem to have a history of quick promotions, with only a few months in a role before being promoted to a management role. What is the secret to your success?

A basketball coach once told me that in order to get better, you have to play against the best. What has made me successful has been not being the smartest person in the room. I’ve always loved to learn, and I always wanted to be around people that I could learn from.

At Cloudwords, every time a new AE came on board, I’d call them and get to know them. I would shadow their calls. I would pay attention to their words and the things prospects picked up on. I learned to personalize based on the conversation I was having. I’d hear words that were used for specific markets or industries and use those in my calls and emails.

When I got promoted to AE at Act-On, I met with the three best AEs and learned about their process. That desire to learn and improve is so important.


What advice do you have for SDRs who are struggling with their next move, or feel like they’ve been stuck in the role? Do you have any quick fixes or suggestions?

I would suggest that anyone in sales align themselves very closely to their leaders. If you don’t have a mentor or an advocate, find one. I truly believe that any manager or director that’s worth their dime will be a mentor. If they can’t, they should help you find someone. We live in a highly connected world. Cold email people and ask them their opinions on approach or process based on their own experience.

I created a career map for myself. It helps me understand what I need to do within each career bucket to get to the next level. If your company doesn’t do it for you, create your own career development plan and let that guide you.


Your LinkedIn profile suggests you know your numbers, which is a piece of advice I’ve heard from many sales managers. Walk me through what you were doing during those times when you were crushing your quota on a regular basis?

My style is not going to be the same as anyone else, so above all, I’d repeat advice given to me: know how you learn.

When I first started, I focused on activities. Looking at raw data should work well to start. Then, I took it one level deeper. I started looking at conversion rates. What were my call to connect ratios? At what time of day? For what titles?

Then I’d start to personalize emails based on data available to me. All my emails, follow ups, and customer stories would be relevant to a tech stack, for example. I also developed my own pipeline from LinkedIn and other sources. At any given time, I had 300 names that I’d be able to reach out to. Then I had another 100 names of just follow-ups.

Finally, I’d be persistent in my outreach. I’d have fun and inject my personality, and I’d follow up with people to the 31st day – I had 6 emails and 20 calls in 31 days. I got a lot of people that agreed to a meeting just because I was persistent.


What are some of your sales management strategies? What tactics do you use to motivate your reps, keep their jobs fresh, or encourage them during difficult times?

Managers need to get to know their reps. I used to work for a company that offered a day off if we met our goals, but I never wanted that. As a manager, however, I took a poll and a majority of my team wanted a day off when they hit their targets.

Personal development is huge. It can be a repetitive job. One thing I’m working on with my team now is how do they build up their own personal brand. We work together on a personal value proposition, and we provide feedback. I connect with my peers on how to get my team more involved in what they do, and it may be as simple as a lunch where we share battle stories.

If the team is having a bad day, get everyone out of the office immediately. The day’s a wash. You have to know your people.


Let’s talk about being a woman in sales and sales management. Do you think women in sales face unique advantages or challenges? If so, what are they?

I don’t think I realized what it meant to be a woman in a professional context until recently. My director said to me at one point that women do better on the phone. People say women talk more, but when you dig into the data, it’s not that women talk just to talk, they’re providing value and making a point.

As a woman in tech sales, I have to talk myself up and repeat some affirmations before walking out the door every day. Affirming myself has helped me a lot because there’s a chance that I’m going to be seen as less than because I don’t fit some norm. It could be a challenge if you don’t have support, or don’t know where to get it. Seek that out if you don’t already have it.


Thanks so much for your time, Gabrielle, and for all the great insight! That’s it for this time, folks. Check back next month when we interview yet another sales leader.

In the meantime, make sure to download our free e-book – Good Sales vs. Bad Sales – or click the button below to learn how the world’s leading personalized selling platform can help your business accelerate sales and increase revenue.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s