The software and technology landscape around you is changing rapidly, which means your sales career too.
But to accelerate your sales career, you need to know the 3 secrets to being a good salesperson and balancing risk and reward.
That's how I did it, and here's what you guys need to know to do too.

The 3 Secrets to Being a Good Salesperson and Succeeding in Your Sales Career

Step 1: Find out what you want for your sales career

I started my professional sales career at HubSpot in 2012.
And as I learned about the product and managing a sales process, I became increasingly interested in strategy.

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How could I produce more with the same effort?
I knew that call analytics focused on both qualification and closure – they boiled down to that.
But I also learned that the biggest lame excuse was “no time, too hard”.
HubSpot asked customers to invest heavily in blogs. The tricky thing was that many companies didn't have a professional committed to writing regularly or most volunteered with the best intentions of writing and then gave up.

How a Simple Playbook Helped Me Sell Surprisingly Easier

Interests outside my goal led me to work with colleagues in customer training, product marketing, and channel sales .
One of our channel partners created a survey asking about a customer's buyer personality.
We then turned the results into a step-by-step playbook on everything a customer would need to do to earn using Inbound Marketing .
It included an outline of the first 9 blog posts a client should write.
One of the partners used this to sell their content writing services.
They helped me use it to close deals where customers were sensitive to the unknown challenges of blogging.
O Content Marketers Blueprint helped me close several deals during a difficult time at HubSpot. Which, of course, was great for my sales career.
After 6 years of registration growth, the “Lead Fiscal Cliff” took place. Lead flow died and, for the first time in my tenure, teams lost their quotas.
A year later, 3 out of 10 members of my sales team were still with me.
Strategies like Blueprint helped me close the deal needed to earn my stay.
This experience, along with some other innovative efforts, led me to be more interested in our sales and marketing alignment mechanics than my own pipeline .
Driving the sales machine excited me more than the search for individual businesses. That was another great lesson that helped me a lot in my sales career.

As I, together with HubSpot, evolved (you'll see how I played with a lot of ideas)

At that time, HubSpot wanted to get into the sales productivity software game and was testing different product ideas.
The AtQuota failed, but the Signals (now known as HubSpot Sales) did it.
Together with another sales colleague, Mike Pici , I had the opportunity, from an early age, to be part of the brainstorming and sales of these fledgling products.
It was the most exciting and rewarding experience I had during my sales career at HubSpot.
And, after a while, my colleague joined the full-time product team to help sell and figure out what to sell in what would become the HubSpot sales package.
Still, in the core business pipeline, I was jealous of the quick learning and high day-to-day variation Mike was experiencing.
He was selling an immature software tool and taking all the closed-lost-and- churn reasons back into the product to make it better.
After a while, the product matured to a state where people in high volumes were buying without a representative.
The following year, Mike built a sales team and worked with Mark Roberge to innovate in compensation, strategy, hiring, and messaging.
I, on the other hand, was doing very well in the core business pipeline.
Software sales can be profitable. If I continued to do well, I would have a good chance to change my sales career and pursue future sales management opportunities. That didn't cheer me up very much.
I started thinking about the idea of ​​traveling the world and working remotely in my role as an account executive (AE).
I thought about Business School, enterprise sales , moving to New York, something to fill a hole I felt in my job.
However, each of these was a Band-Aid. Finally, I recognized that I wanted what Mike had – an opportunity to use my sales skills and creativity to help develop a sales machine and products to bring to market.
Another opportunity similar to Mike's was unlikely to arise internally, so I opened my mind to new horizons in my sales career.

Step 2: Find out if there's a way to get it faster

Around this time, I started reading Jason Lemkin on Quora and then SaaStr.
Discover the “Stretch VP” Jason's posts introduced me to the concept of the “ Stretch VP ” – a person who could enter a company at an early stage with limited experience and grow with that company as a sales leader.
Boom! It opened my mind then.
There was a precedent for quick follow-up to sales leadership. (Now, reading closer, I should have been discouraged. My experience was still too limited to fit your definitions, but sometimes we hear what we want to hear.)

The way to be a Stretch VP (the options I had)

With Mike as inspiration and Jason showing me that there was a precedent, I turned to former HubSpot vice president – ​​who went from $0 to $100 million – Mark Robberge.
We had lunch at the Cheesecake Factory, and I told Mark I wanted to accelerate the sales lead.
He told me,
You are a representative at an IPO company. You have three options:

<![if !supportLists]>· <![endif]>Go to company B -> Pre-IPO to manage,

<![if !supportLists]>· <![endif]>Be a director in an A, OR stage business

<![if !supportLists]>· <![endif]>Get into the early stages, try to be the number 1 rep and try to maintain the sales leadership role as you grow.

Finally, the “how”.
Now I knew what I wanted, there was a precedent and a general path to get there.
Simply he had revealed to me one of the 3 secrets to be a good salesperson and change my career.

Step 3: Get lucky (also known as jumping in)

So, pure luck.
I shared my new ambitions with some close friends at HubSpot.
Jonathan Kim, a former HubSpotter who had just released a beta version of a product, approached Mike and asked for advice on how to sell to the leads he got from a Product Hunt launch.
Mike knew this was why I was hungry and introduced me instead.
One afternoon I went to the WeWork that Jonathan was using as an office, and we squeezed into a phone booth and called all of his contacts.
It was torture for him, hearing me ask qualifying questions of these people. They signed up to try your product and didn't deal with a salesperson (classic product person, right?).
Then, hours after one of our sales demos , a company from Australia decided to buy our biggest package.
That would have been a solid deal at HubSpot.
I thought to myself, “Man, Jonathan is smart! We pretty much just sell an idea. ”
That night, walking home, I realized that he had found a real problem to solve. Clearly, it was time for me to learn to take the risk. Time to stretch.
It's been 3 years since I joined Appcues. We are growing faster than ever and the sales organization reaches 10.
Jonathan and Jackson – the founders of Appcues – and I continue to thrive together. We are still early and most of this journey has yet to unfold.

Here is my #1 homework for you to change your sales career

If this story sounds similar to you – if you feel it's time to take a similar risk – start here.
Someone did what you are trying to do. Find them.
Find companies that run the parts you need to run six or nine months from now.
Look for similarities in buyer, ACV, and go-to-market strategy. I ran into InVision when we were setting up a business plan and we pestered their VP of sales to the point where he introduced me to a Google sales leader group called Modern Sales Pros.
This company's content archives have been a weekly resource for me ever since!

<![if !supportLists]>1. <![endif]>You want to get to the big fish, find someone who did it.

<![if !supportLists]>2. <![endif]>Launching a new product? Find a company with a successful launch.

<![if !supportLists]>3. <![endif]>Building a Hiring a Plan? Look for someone willing to share your model.

There is always someone who has a lot to help you throughout your sales career and is ready to pay you back.
But you have to ask.

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