Autopilot HQ reveals the 3 key reasons for their rocketship growth

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While there is no silver bullet for success in sales, there are tried and tested sales strategies, so you don’t have to reinvent the wheel. The Secret Sauce to Sales by Freshsales features top sales leaders across industries who give you inside access to their sales methodologies. In this edition, we reveal the reasons for Autopilot HQ’s growth. 

James O’Connor is the Director of Sales at Autopilot HQ—a visual marketing automation software that lets you automate customer journeys across multiple applications. Used by thousands of customers like Microsoft, Greenpeace, Lean In, Typeform and their ilk, the tool has over thousands of customers, signed up tens of thousands of free trialists, and experienced double-digit month-over-month revenue growth.

After joining Autopilot HQ as one of the first sales reps, James now heads a team of 5 and oversees all new business operations in the organization. We got to sit down for a chat about his sales success story in AutopilotHQ.

How did Autopilot HQ happen for you? Tell us about your transition to this role.

Prior to this, I was working at a different tech company when I got to know about Autopilot HQ. It was a small team at that time, and I had some experience with marketing automation systems in a few roles before that.

So I sat down with the team and ended up meeting Michael Sharkey, our CEO, as well. He showed me the technology, and I was blown away by what they were working on—knowing some of the other tools in the space and how hard they can be to use.

I was really excited by the opportunity to get behind this product and jump on board. I ended up accepting a role as their very first business development rep.

You have seen Autopilot HQ through its rocketship growth in a competitive market. What do you think are the reasons for Autopilot’s success?

Our visual journey builder, free trial capability, and our competitive pricing. These would be my top three things that have led to our success.

Visual journey builder: The sheer ease-of-use and our intuitive UI that works the way your brain works.

Free trial: The ability to try before you buy without having to make any long-term commitments.

Pricing: Affordable pricing that is within reach of every business.

The visual journey builder is the number one thing that has helped me from a sales perspective. In a matter of minutes, you can easily show a potential customer some pretty interesting customer journeys. While there are a lot of flow-based workflow or automation tools out there, I’m yet to see one that is better than Autopilot. We have the most simple and visual approach.

I have talked to many prospects who have had the visuals up on their screens and have been asked by others what it was all about. You can be confident that the canvas is going to generate some buzz within the workplace simply because of the visual nature of it.

And that can go a long way in getting you more visibility across other individuals and teams in an organization; without you having to scale as quickly as you would in a normal sales cycle.

How do you think the free trial offering has been crucial to Autopilot’s success?

I honestly think it’s mission-critical. I always encourage anybody who is looking at any software to really push the company and ask for their very own demo account, even if only for a few days.

I don’t think anybody should be purchasing software unless they have actually logged in and tried the product. The ability to prove value before purchasing makes the decision very easy.

In today’s software world, I think it’s almost crazy that you wouldn’t get a chance to click around or work with the software before making a monetary commitment.

When you are forced to put down your credit card to try a software, it makes you feel under pressure —  you can’t test it all out at the risk of being charged. With a ticking clock, it’s just not possible to evaluate and make a decision within 14-30 days simply because your credit card is on file.

You don’t look at it quite the same way you do with a free trial. You actually take your time, assess the software, and talk to your team about working out the new software then.

Clearly, Autopilot’s pricing has given it an edge over other tools. How do you leverage this to close deals when you’re evaluated against the others?

It helps us frame where exactly we fit in the marketplace.

Ultimately, somebody is always excited about saving some money.

When you are able to accomplish everything that the customer wants to do, and the tool is one-third of the cost of the all-in-one providers, it’s fairly easy to sell. And once that’s done, it paves the way for selling internally as well — by using the existing success story of a team within the same organization.

Compared to the rest of the providers, we do find that we are very competitive for the space and that really makes us one of the top choices for people. Also the fact that we can do everything we want or they want on Autopilot.  

Our prospects do have to think a little differently as opposed to when they consider a tool like Marketo. For instance, you’d have to use a third-party tool with Autopilot for a few features while Marketo would offer the same within the tool. However, our pricing makes the difference when prospects choose between us and a competitor. It definitely speeds up the sales cycle.

Related: How Chargebee leveraged the freemium model and grew by 4X in revenue

How do you pitch the tool and differentiate it from the others in the field?

Autopilot is a tool that can solve a couple problems for you really quickly. Our trial users are mostly signing up either because it’s their first time with a marketing automation tool or they find other tools too complicated or expensive. And when they do, they find that they can build a lot of their use cases in a free trial capacity within Autopilot.

The free trial lets them get a complete sense of how the tool works in full production even before they make any commitments. Added to that, we also offer the flexibility of monthly pricing — meaning, they don’t have to lock into a long annual contract.

As far as sales differentiation is concerned, the one thing that our customers really like is the ease and speed with which they can iterate automations they are running in Autopilot.

With other marketing automation platforms, once you get everything up and running, it’s hard to make iterations after just a few months of installation. Autopilot gives you the flexibility to put something into effect, review the results and make changes even if it’s only been a couple months since implementation.

It’s as easy to make the changes as it is to wonder how the changes would reflect. Autopilot moves with the pace of your business.

With a six-member team, how do you keep up with the pace of the business? What sort of sales process do you have in place?

Our customer base ranges from enterprises like Microsoft to SMBs. My team mostly handles larger accounts while we have a few automations in place for some of our lower plans.

The smaller accounts get access to webinars and get their questions answered. Though they don’t get a direct representative assigned to them, they still have somebody to help them through it.

With a predominantly inbound sales model, our leads come from our website, trial, even through the traditional contact request form. The key aspect for my team is to focus on leveraging Autopilot to solve the problems that the customer presents.

By helping the customer configure their trial account, our team gets to show other members of the organization how Autopilot really functions should they decide to purchase.

About the sales process — once a lead is assigned to a sales rep through the round-robin, typically, they get in touch with the prospect to do an introduction call to get an understanding of their business and why they signed up for the trial. It’s followed by a secondary meeting where they would actually sit down and configure their account. It acts as a working session to help them get familiar with the platform and have them build the first few automations.

From then on, our reps are responsible for whatever validating steps are needed to help them make the most of the technology. Also, our sales cycle is usually anywhere between 20 and 60 days, with a free trial for 30 days.

Autopilot HQ Funding
Autopilot HQ Funding

You have customers of varying organization sizes. Who would you recommend as the ideal buyer?

I think the ideal buyer or ideal customer for us is really somebody who’s looking to do marketing automation a little differently. They are customer journey marketers who want to automate the repetitive tasks in their entire lifecycle. They want to communicate in more contextual and personal ways.

It’s also people who want to use best-of-breed applications like Instapage or Unbounce for landing pages, Segment for their data, or be able to use a BI platform like Heap Analytics, and even leverage our API to push data to a tool like that.

Someone who’s looking for marketing automation to play a role by connecting all those applications — with marketing technology stack and Autopilot being the core of that.

By title, traditionally, the buyer would be the CMO or Director or VP of marketing. Mostly, we see the marketing manager as the one who signs up for the trial and then we ultimately work through the organization from there.

Autopilot Anniversary Party
Autopilot HQ Anniversary Party

What does a typical day look like for your team?

A typical day involves taking a look at their calendars to see what kind of calls have been scheduled. We use Calendly for that. Whether it’s a new lead who signed up for a trial, or introductory calls or even secondary meetings, it’s automatically scheduled in our calendars.

The latter part of the day is to look at new leads or opportunities that need to be seen from a fresh lead perspective, or even following up with active deals.

If there are leads who are coming to the end of their trial, figuring out their needs and doing what it takes to close the deal. It’s really all about meeting with people and providing them with the right solutions.

What about you? How do you pave the way for your team?

I have a couple of priorities. I make sure my team stays on top of the leads coming in, and create a healthy pipeline so we can forecast how we will be meeting targets that month. Then, I strategically help them out with any sales cycles that they are actively running and need my assistance.

Apart from that, I’m mostly getting into calls at a director-level to talk through different hurdles that people have while thinking about purchasing the product.

Autopilot HQ Team
Autopilot HQ Team

While making a sale, what is the most common obstacle that you have come across? How do you overcome that?

In my opinion, it is when a buyer fails to understand what exactly they are purchasing and how it works. How are their first 30-90 days going to look like?

How do they prove ROI by making this purchase?

So we take a step back to understand their business and show them what these automations will do and how they will see a positive impact on their business in the long term. We find out how their key metrics fare at the moment and why they are looking at Autopilot.

Then, we show how some of our other customers are having success, such as, ‘If you were to do this, you’ll see an X amount increase in the first 90 days based on the performance history.’

I think when it comes to technology, it’s really all about working with our great support team. By taking a look at the problem, we learn if something is working or not on their side of the trial or within our platform.

And almost every time, there are just a few slight tweaks that need to be made to help them overcome their issue or something that they can easily change to make Autopilot more compatible with a specific integration.

Another relatively common question we come across is if their integration is working correctly. Thankfully, our trial helps people find any kinks that they need to work out with regards to integration.

Autopilot HQ Co-Founders | Mike Sharkey, Chris Sharkey, Peter Sharkey
The Co-Founders of Autopilot HQ – The Sharkey Brothers (Chris, Mike, and Peter)

As a sales leader, what do you think is the one misguided practice in sales?

Pushing a deal that doesn’t really fit with the technology you are selling.

Depending on how your month or quarter is going, I think every salesperson has fallen victim to it at some point. I think you need to be able to recognize when something may just not be the best fit — even if part of the use case looks good but the rest of it is just forcing it.

A lot of times, people go ahead with bad deals and because we are all good at selling, the deal is done too. Ultimately, it can cause a lot of problems for the success of the organization or even the support team in the long term. While being short-sighted by getting a deal will get many excited about the new revenue, it fails in the end.

You have to look at how it will work out in the long term. Is this person going to be successful in a couple years? Will the success team be easily able to implement the software?

In my opinion, sales reps sometimes don’t consider the long-term implications of working with somebody.

What do you look for in a new hire?

Somebody who is focused on confidently selling the solution and solving problems using technology. You should be able to carry out a demonstration of the software during a deal and own the entire sales cycle.

We don’t have a sales engineer to do the demo for you or an entry-level sales person who will qualify the opportunity for you. You need to be able to go out and make your own opportunities.

Ultimately, someone who can master the product and help the customers solve their problems by leveraging Autopilot.

Your favorite productivity hacks

I’ve always been a fan of Rapportive. It’s a tool that lets you view somebody’s LinkedIn profile just by hovering over their email address. And Calendly. It saves me a ton of time by allowing people to access my calendar directly and book meetings.

Sales Productivity Tools

Related: Behind the Scenes of Calendly Sales Growth

Key metrics you focus on

The number of open leads, revenue closed, and pipeline generated.

Key Metrics to measure - Autopilot

What would you recommend for sales reads?

I always recommend Solution Selling by Michael T Bosworth and the “The Challenger Sale — Taking control of the customer conversation” by Brent Adamson and Matthew Dixon. Both are pretty easy reads, and great if you’re getting into software for the first time.

Another book called Winning Ugly — it’s actually not a sales read at all but it’s by Brad Gilbert, a tennis player, and Steve Jamison. Although it’s about tennis, It helps you get a bit of understanding about the competitive streak of being a salesperson.

Top Sales Book Recommendations - James O' Connor

A motto your team likes to follow

Always do right by the customer.


Freshsales is a sales CRM built to help you stop juggling multiple tools. It’s ideal for small businesses and refreshing for enterprises. 

While there is no silver bullet for success in sales, there are tried and tested sales strategies so you won’t have to reinvent the wheel. Secret Sauce to Sales by Freshsales features top sales leaders across industries and gives you access to their sales methodologies. Drop us a line in the comments or shoot an email to nivas.ravichandran@freshworks.com with your suggestions.

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