Risk vs. Reward: 3 Secrets That Will Change the Way You Think About Your Software Sales Career Path

In order to keep up with the changing software and technology landscape, you have to balance risk versus reward.  

I’ve learned a lot, and this is what you need to know if you want to do it too.

Step 1: Determine your software sales career path for software sales.

The more I learned about the product and how to run a sales process, the more interested I became in sales strategy.

In my software sales career path, I was feeling overwhelmed by the amount of work I had to do, so I needed a solution

I learned that the biggest reason people don’t buy is that they can’t make time to do it, or find it too hard.

HubSpot had a requirement that customers blog regularly. What was tricky is they didn’t have someone committed to blogging or most people only signed up with the best intentions of writing and then dropped the ball.

How a simple playbook helped me sell surprisingly easier

I work with colleagues in Customer Training, Product Marketing, and Channel Sales. One of our Channel Partners created a survey asking about the buyer persona of customers. The results were turned into an actionable playbook for how to win using inbound marketing.

The Content Marketers Blueprint helped me close several deals during a tough time at HubSpot. I was able to use it for content writing services and help people with their blogging.

After a year of up-and-to-the-right signup growth, the Lead Fiscal Cliff occurred. I noticed that lead flow died for the first time in my tenure as an entrepreneur and teams missed quota. A year later, 3 out of 10 members from my sales team were still around because we had to close leads needed to earn our stay.

This experience in software sales career path led me to be more interested in our sales alignment mechanics than my own funnel. Seeing the results of leveraging a well-oiled machine excited me more than trying to make individual deals with customers.

How I evolved with Hubspot

When HubSpot wanted to get into the sales productivity software game, they realized that AtQuota didn’t make it. Signals did.

One of the best experiences I had at HubSpot was when Mike Pici and I got to be part of brainstorming these new products. It really felt like we were doing something important.

Eventually, my colleague became a part of the product team full-time to help sell and figure out what to sell in our HubSpot suite.

Despite the fact that he was burdened by many responsibilities his software sales career path, Mike’s product matured and people were buying without a rep.

Over the next year, Mike built a sales team and worked with Mark Roberge to come up with new compensation plans. They also experimented on hiring strategies as well as messaging.

I was doing well in the core business funnel, and I thought that if I stayed on this path, it would lead to a great opportunity.

Eventually, I began to think about other opportunities in my career. This included business school and moving from Account Executive (AE) role into a different type of sales position.

I wanted what Mike had. I wanted to help develop a product and sales machine, so that when it was time for me to leave the company, my successor would be in good shape.

I was looking for a new opportunity and found one, but it wasn’t available at my company.

Step 2: Determine whether there is a method to obtain it more quickly.

I started reading Jason Lemkin on Quora and SaaStr around the same time.

Discovering “Stretch VP”

Jason introduced me to the idea of a “Stretch VP”, someone that can come into an early-stage company with limited experience and grow as their sales leader.

Boom! It hit me right then.

I should have been discouraged when he said that previous experience was a better indicator of success than raw talent. I had only experienced one company and didn’t feel like it would be enough to confirm his theory.

The road to being a stretch VP (the options I had)

After talking with Jason and Mike, I decided to talk to HubSpot’s former stretch VP who went $0 – $100M. We had lunch at Cheesecake Factory and talked about my future in sales leadership.

He told me,

“You’re a rep at an IPO company. You have three options: Go to a B —> Pre-IPO company to manage, Be a director at an A stage business, OR, Dive in at seed stage, try to be rep #1, and attempt to maintain the sales leadership role as you grow.”

If you’re looking for a good company to manage, go to one that is pre-IPO.

If you want to be a director at an A stage company, or

When you start up, try to be the first rep and maintain that leadership position as you grow.

I now knew what I wanted, there was a precedent set by other companies, and it seemed like the best path for me to take.

Step 3: Get lucky and put yourself out there

Then, pure luck.

I had shared my new ambitions in my software sales career path with a few close friends at HubSpot, and one of them reached out to me when he was getting some leads from Product Hunt. He knew that I wanted this position so Mike introduced us.

One afternoon, I went to the WeWork office that Jonathan was using and we called all of his leads together into a phone booth.

It was torture for him to hear me ask qualifying questions while we talked with the people who had signed up to try his product. He’s a classic salesman, so hearing them talk without trying anything is just too much.

The company from Australia bought our largest package after we gave a sales demo. This would have been a good deal at HubSpot.

I was so excited with my software sales career path when I realized that Jonathan had just sold an idea. We were able to come up with a solution.

That night, when I was hanging out at home and he told me about the problem he had found to solve, it became clear that it was time for me to learn how take risks. Time for me to stretch.

It’s been 3+ years since I joined Appcues. We’re growing faster than ever and the sales team is up to 10 people. Jonathan, Jackson–the founders of this company—and I are still working well together.

Here’s My #1 Tip for YOU

If you’re ready to take the risk, start here.

It seems like this article is about how it’s time for companies to hire more diverse candidates during hiring process in order to increase work environment diversity. I would say that “This story resonates with me” or something similar could be a good paraphrase of what they are trying to get across at the end of the paragraph where they speak directly towards readers and tell them if this topic has made an impact on their life then maybe it should make an impact on theirs too!

The internet is a great resource for finding people who have done what you’re trying to do. They can provide guidance and advice that might help with your situation.

Find companies that are similar to your company and see what they’re doing. I found InVision because we were looking for a big account strategy, and their VP of Sales introduced me to Modern Sales Pros on Google Groups.

I’ve been reading their archives every week since I found them!

If you want to hire someone who is more experienced, find somebody who has just gone upmarket.

2) Launch a new product? Find an existing company with similar success.

If you’re looking for a template, try finding someone who’s willing to share theirs.

You have to go out of your way in order to find these people.


Need Help Automating Your Sales Prospecting Process?

LeadFuze gives you all the data you need to find ideal leads, including full contact information.

Go through a variety of filters to zero in on the leads you want to reach. This is crazy specific, but you could find all the people that match the following: 

  • A company in the Financial Services or Banking industry
  • Who have more than 10 employees
  • That spend money on Adwords
  • Who use Hubspot
  • Who currently have job openings for marketing help
  • With the role of HR Manager
  • That has only been in this role for less than 1 year
Just to give you an idea. 😀



    • A company in the Financial Services or Banking industry
    • Who have more than 10 employees
    • That spend money on Adwords
    • Who use Hubspot
    • Who currently have job openings for marketing help
    • With the role of HR Manager
    • That has only been in this role for less than 1 year
Editors Note:

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Justin McGill
About Author: Justin McGill
This post was written by Content at Scale, a solution that uses AI + a team of optimization specialists to publish hundreds of high quality, SEO optimized content straight to your blog. It’s the first and only solution that allows you to truly scale content marketing.