Growing a Sales Automation Platform from 0 to Hundreds of Users in Under 2 Quarters

Sales Automation Swiss Army Knife and CRM
Ian Reynolds


Founders: 2

Employees: 50

Users: 500+ Paid

Who Are You & What Business Did You Start?

My name is Ian Reynolds, I am the owner at OnCourse Sales Automation, a sales automation platform with built in CRM and marketing automation functionality. I am also a partner at a software engineering services firm that builds software for companies from startups to Fortune 500 firms. 


How Did You Come up with the Idea?

OnCourse Sales Automation started out of a pain point we were facing at our service business. We were paying around ~80k a year for a handful of tools including: email automation, CRM (Salesforce), a phone dialer, sms marketing, and marketing automation tools (hubspot). As we were scaling certain aspects of our sales team and marketing efforts we were having a very tough time managing all the tools and having them talk to each other in a way that let us measure communication and sales performance in one clean pane of glass. We even had our engineers build out special integrations to try and solve this problem; it just didn’t work the way we needed. We ultimately decided to make a massive investment and solve this long standing problem for good. OnCourse Sales Automation was the result. 


Describe the Process of Launching the Business

In contrast to a big wind up and announcement we intentionally launched rather unceremoniously. We had been using the tool internally for about half a year and were more than confident that it would be a hit once we started selling it. It has also been our experience that big launch plans can often lead to big disappointments when you don’t plan the party properly. The ROI for a launch like this didn’t make sense in our view so we just put out a press release and had some pizza at the office. We looked at the ROI of big splash launch economics vs putting that in long term marketing and sales results and it has worked out better to reinvest the money.


Since Launch What Has Worked to Attract Customers?

We've used a very traditional SDR model for hunting and an AE model for closing. There is a delay in generating opportunities and closing them right away with a new product so the senior sales team members started earlier than the SDRs and we figured out some process items before scaling up the sales team. This has worked well and will only get more efficient over time. We are also finding a lot of value with traditional search engine marketing and ads. Millions of google searches per day give us plenty of opportunity to serve relevant information about our brand to customers seeking info. 


Describe a Moment Where You Had to Overcome a Challenge – Before or After Launch

We had a really big spike in infrastructure utilization because of the rapid demand (and great work of our sales team’s aggressively leveraging the tool). The kid gloves came off fast so we had to scale the infrastructure more quickly than wed planned to. We have a Kubernetes setup and hand planned to setup certain scaling elements after wed completing some other testing components but we had to make a tough call and have the team to work through a few weekends to accelerate that schedule. Great problem to have, but also a terrible one because it meant we had to periodically take the tool down during low utilization hours and peoples weekend plans were ruined. You would be very surprised at the times sales team members will log into a tool to work. 


What Platforms Do You Use for Your Business?

We are a cloud first company. Meaning, we want to reduce our reliance on physical infrastructure that we need to support. There are cost benefits to this and it increases the teams ability to focus on solving problems that are core to our clients and the business rather than operational penny pinching. We make heavy use of Google/Microsoft products for productivity. We make aggressive use of the open source version of Rocket.Chat, a slack alternative for team communication and have various groups setup on WhatsApp so that our global team is always a quick text away from each other. 


Advice for Other Entrepreneurs Who Are Just Starting out

I think this is a difficult question to answer. Businesses are a lot like fingerprints, they are unique, no one else has exactly what you have. We try to take a philosophical approach to everything we do that considers what the very biggest businesses are doing. We want to do things in a way that consider best practices but also don’t create a solution that is too complex from the start. We want fundamentally simple tools we can add complexity to later – we don’t know what people want until we get them into the tool so we have to limit our creativity. Not building a Maserati out of the gate is a great way to avoid over investing. While we have built a super powerful tool, that is only getting better, we've boiled these very complex parts into simple elements and its worked super well. 


Where Can We Go to Learn More About Your Company?

Check us out at