I contacted Monica when we were both working at Gartner, knowing that she’d have good stories and insights from her days selling door-to-door. What I didn’t expect was the level of service-mindedness which accompanied her success throughout her career.

Monica blends competitiveness with client focus; which has made for a highly successful career in one of the better sales-focused organizations in the world.

You can read Monica’s full biography here

Jamie: Monica, what have you found most fulfilling about your career thus far?

Monica: What I found most fulfilling when I was in a sales role was building relationships with my clients and prospects. My college major was Hospitality Management, and I always saw myself having a career in that industry. I found that the element of client experience that I loved about hospitality was part of a sales role as well. And let’s be honest, it didn’t hurt that a sales career paid much better too. But overall, what I found most fulfilling about my sales career was building trusted relationships with my clients and prospects. And to me, there was nothing more fulfilling than to see the insight, tool, or coaching that I sold them lead to my client’s success.  

Jamie: Do you think that service-mindedness made you a better salesperson or contributed to your success?

Monica: Yes, absolutely. 

Although it also made me challenge things as well. When you are in sales, you are constantly striving towards a number or goal. I would always challenge myself when creating each proposal. I wanted to ensure that whatever I was positioning was truly the best solution to help clients achieve their priorities. 

Sometimes that led to not getting the growth deal that month or quarter because we still needed time to uncover the best solution to meet their needs. But I took a lot of pride in doing what was best for my client, and maintaining that trust was most important.   

Jamie: Do you think that it negatively affected your bottom-line results?

Monica: No, I don’t think so. When you sell a good product, it definitely helps. I was successful in my sales roles with Southwestern Company (top 5%) and Gartner (Club 300; top 5%). 

If I didn’t prioritize building trusted relationships with my clients, then I definitely wouldn’t have been successful. I would never position something that didn’t have a clear business case and ROI for my client. 

I had to ensure I was putting their needs over my quota. 

Jamie: What was the thing that made you want to be in sales in the first place?

Monica: I’m a very competitive person, and there’s always a competition going on within sales teams – that was something that I really liked. Also, in sales, you have unlimited earning potential, which was something that drove me as well. So the competitive aspect and earning potential are probably the two main things that drove me into a sales role in college with Southwestern Company (door-to-door sales) and after college with Gartner.

Jamie: In a largely sales-led arena, how are salespeople compensated versus their non-sales peers?

Monica: It depends on the organization, but in my experience, I’ve seen SUCCESSFUL salespeople compensated more when they have an uncapped earning potential. 

I’d assume that in many organizations, salespeople have the opportunity to be more financially successful than those in non-sales roles. However, on the other side, if the sales executive has a challenging year, there’s no guarantee. 

Non-sales roles may have a larger guaranteed salary, with less opportunity to go above and beyond that level of compensation. Salespeople have a higher earning potential, but there are also risks that go along with that.

Jamie: Do you believe that an aspiring salesperson should be looking for an organization that is sales-centred?

Monica: Yes, 

I would recommend that an aspiring salesperson looks for an organization that is sales-centred. When you think about the business partners aligned to support you as a sales executive, you want them to be willing to prioritize what you need to help a client and close the deal. 

Being a sales-centred organization allows the salesperson to more easily do things like schedule a proof of concept call with the right resource and in a timely manner. The urgency and levels of quality may not be there if the organization is not sales-centred. 

Jamie: What skills do you believe that someone should exhibit naturally to get into sales?

Monica: I believe that mindset is most important. A salesperson cannot be afraid or feel rejected when they hear the word “no.” They cannot run from challenges or adversity. They need to understand that success doesn’t happen overnight. You may be having a really challenging day, week, month, or even year. But if you maintain the right mindset and focus on doing the right things that are within your control, the results will follow in the end. That mindset is huge for a salesperson to be successful.

Jamie: Is there a specific personality type that is best suited to sales?

Monica: I don’t believe so. I think often, people assume most salespeople are extroverts, but I know I’m personally more introverted, and I’ve done just fine in sales. 

Jamie: Would you recommend that anybody goes into advisory sales specifically?

Monica: I don’t know about anybody. I think any personality type can do well, but I also believe that they need to have the right traits to be successful in sales.

Jamie: What skills are needed in sales?

Monica: I think somebody who is driven, who works hard, and who has the right business acumen to be able to listen and have the right conversations. Somebody who thinks strategically and isn’t just looking for a quick win, but understands the importance of long-term success. Those are things that are important for salespeople in advisory sales because you’re not just selling something and then leaving. You sell them something and then need to ensure they’re making the most of the product you’ve sold them. Each year you’re going and asking for a continued partnership, and you need to have that long-term view. It’s not about short-term wins, but thinking about the longer-term strategy to enable the client to succeed leveraging your product.

Jamie: What are the biggest challenges of winning business in advisory sales?

Monica: It depends on who you’re selling to. If you’re not selling to someone who has the power or budget to make a decision, then that can be challenging. You have to either involve power in the decision-making process or ensure the person you’re selling to is convicted enough that they can sell to power themselves.  

Jamie: How do you go about navigating that organization with complexity and power structure?

Monica: I think it goes back to having a strong relationship with the person you’re working with. If they understand the value in what you’re proposing, and you’re working from the same side of the table, it makes it much easier. Being aligned on the business case and ROI of what you’re proposing will go a long way.      

I remember I worked with a client who was convicted in the proposal and the value we could bring to him and his organization. He wasn’t able to make a decision to move forward, and needed CEO approval. He and I partnered together to craft a business case that would resonate with his CEO and clearly convey the value we’d bring to his organization. My goal was to help build confidence and conviction so that was clear when the ask was made. 

Jamie: How do you go about getting a job at the advisory sales industry?

Monica: You figure out the traits that they want and then you make sure that you show the traits in your interview. [laughs]

I mean to be honest, that’s what I did.

I believe it’s important to understand what the company is looking for and what type of person is successful in the role. The first thing is to be honest with yourself and ask, “Are those traits that I have? Can I be successful here because that’s what they’re looking for? Do I truly have those?”

 If you do, you need to be able to highlight those throughout the interview process using stories and examples. If you don’t, then you should probably look for another opportunity where you’ll be positioned to succeed.

Jamie: In terms of figuring these values that companies value and would want from you in an interview, how did you go about that process?

Monica: I would just ask. And I’d also do my research on the organization to hypothesize what those values would be if they’re not clearly laid out on their website. You can ask any connections you have within the organization, the recruiter or the hiring manager. It’s not necessarily directly asking, “What traits are you looking for,” but asking questions like, 

“What are the traits that your best salespeople have? What about those who aren’t as successful, where do you feel they had a gap?” It’s a more tactful approach to uncover the insight you’re looking for.

Jamie: What advice would you give to aspiring salespeople?

Monica: It all goes back to the mindset and having the traits necessary to succeed. There are a lot of people who just go into sales because they see dollar signs and get sold on the significant earning potential. But at the end of the day, if you don’t have the right mindset and traits, you will not be set up for long term and sustainable success.  

Jamie: Is there any specific training you’d recommend that aspiring salesperson should look for?

Monica: Honestly, if you’re still in college or university, doing door to door sales is really a strong test on your mindset and perseverance – both important in sales roles. 

It’s a pretty extreme way to go, but I’m confident that if someone can be successful going door-to-door in the summertime (when it’s hot and all their friends are off doing fun things), then probably have the right mindset. Going door to door you learn to focus on the controllables and not be deterred when facing adversity, whether it be getting bitten by a dog, having doors slammed in your face, having your car break down, or selling nothing after 13 hours straight of knocking on doors in the heat of the summer. 

Sales is not an easy career path. You are going to face challenges and adversity along the way, but I found that door to door sales was a good test for me and helped me build success principles for my longer term success. 

I have a lot of little brothers, and I always tell them that they need to go and do internship to get more experience and understand what they’re passionate about. I see a lot of people graduate and not having any idea what they want to do next. Internships help expose you to potential career paths and what would align to your strengths. 

Jamie: If you were starting your career in sales again, what would you do differently?

Monica: Reminding myself from the beginning of my sales career to have patience. It took me a little bit of time to realize that success was not immediate. I would want to remind myself to have patience, remain focused on building strong relationships with my clients and continue executing the best practices that are within my control.  

Jamie: Could you tell me about a time you failed to make a sale, but you learned something really valuable?

Monica: It was when I first started in my sales role post college. I had built a pretty good relationship with the client. We had good conversations, but hadn’t quite built up that trust yet. The client did not end up moving forward with my proposal and looking back I realized that I didn’t do a great job building out the business case to show the value it would bring to the overall organization and to the client himself. I wasn’t digging in enough to strategize with the client and wasn’t able to clearly show how the proposal aligned to his priorities.  

Jamie: On the flip side, can you tell me about a time when you succeeded to make a sale, and it showed the skills you developed throughout your career?

Monica: It’s basically the same story but the opposite. I had a really strong and trusted relationship with the client. I understood his objectives, and how his objections enabled the organization to be successful. The client had a particular challenge that we could help him solve to enable his success. By clearly mapping out the business case and ROI, it made the proposal a no brainer.  

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