How to Turbocharge Your Sales Pipeline in 4 Steps

Mike Ryan is Senior Director of Global Demand Generation at project44, a Chicago-based startup that provides a transportation visibility platform for shippers and third-party logistics firms.

Mike discussed how he helped project44 move upmarket and increase its pipeline tenfold at our October 30, 2019 Here’s How Startup Marketing Conference.

In case you’re looking for the quick takeaways, here are our favorite lessons from this presentation:

  • Look for quick wins. For early-stage businesses, these can be key to future success.
  • Take inventory of what’s worked for you in the past. Then, do the research to find out where the market’s headed.
  • Experiment rapidly. Quick, measurable results will enable you to learn faster than your competition.

Curious to hear more about how his team did it? Read on for a complete transcript of his presentation.

I head up the demand generation team at project44, which means I lead our events, digital programs, and marketing operations. Formerly, I was the first Head of Marketing at Keeper Security. I also did product marketing at Uptake and worked for a small IoT company called Hologram.

I’ve been at project44 for about a year. We’re an advanced visibility platform, and we help improve customer experience for companies like Amazon and Walmart as well as third-party logistics companies like Echo Global Logistics and Coyote. We’re a Series C company, and we raised $90 million last year.


I joined little over a year ago, between two fundraises. When I joined, we had already reached “Zero to One.” We had a product-market fit. We raised $45 million. We had fierce competition with FourKites.

We especially had a strong product-market fit with the third-party logistics segment, but the market is very limited in that segment. That meant we needed to go upmarket.

We were tasked with doubling bookings. The market that we wanted to go into was a billion-dollar market.

Going into that market was very challenging and required a lot of changes, so I'll walk through how we actually did that.


Step 1: Look for quick wins

This is true for any employee at a new early stage company: you want to look for quick wins. When I joined, I took an inventory of what we were already doing, and I saw that there was some low-hanging fruit.

For example, I noticed we weren’t doing any search campaigns. I started to build those campaigns for some lower funnel traffic, and in the process I analyzed what programs were working and what weren’t. We discovered a few things.

In the analysis process, we looked into Salesforce to see what the conversion stages were and where things were dropping out of the funnel.

First, we saw that on average, the number of touches for a lead to convert to an opportunity was around eight. For the majority of our leads, we’re only touching them two or three times.

That was a clear quick win for us. By increasing the number of touches in our lead follow ups, we tripled our conversion rate.

Those are a few things we did in the first 30 to 60 days to snag some quick wins. Beyond that, we wanted to figure out what else we weren’t doing and who else we weren’t going after.

Step 2: Perform market analysis

Part of the process of going upmarket was looking at where we had success in the early days of going after this market. We looked at our pipeline and Salesforce to understand some of the customers that we've already won. We talked to analysts at Gartner and International Data Corporation to understand where the market is headed.

We wanted to find the intersection of where we’ve had success, where the market has had success, and what analysts are predicting for the market. This helped us determine our ideal customer profile and target market, and which segments had the highest propensity to buy.

Next, we’d be able to build a road map of where we needed to go as a marketing team.

Step 3: Evaluate the funnel and unit economics

The third part of this process was looking at our funnel, unit economics, and conversion rates. We had to make sure that we were running efficiently before we scaled up and that as we increased our lead and demand generation, things weren’t dropping out of the funnel.

On the unit economics side, we needed to model where we needed to be from a financial perspective. We established our booking targets and then worked backwards to answer a few questions:

  • What should our opportunity conversion rate be?
  • What’s our average deal size?
  • What’s our sales cycle?

Then we could figure out what inputs we needed to hit our goals at the top of the funnel.

Step 4: Experiment, measure, and learn faster than your competition

Next, we started to scale our programs. This is the most challenging part, but if you take all the fundamental steps before this, it makes it a lot easier.

Whether you’re at a B2B or B2C company, I hope you’re doing some form of experimentation. For us, my mentality was that if you’re able to experiment and learn faster than your competition, you’ll have an edge over them.

We did our best to first build a backlog of experiments in a spreadsheet, sourcing ideas from various internal teams, from the sales team to the product team. We looked at what other companies were doing in this space, ranked them, and then decided what was the highest impact, lowest effort experiment we could run.

It took us a week or two to plan each experiment, and then we ran it for a week or two. We always left a week after the experiment wrapped to ensure we were measuring what we were doing. Then, we came to a quick conclusion of whether the experiment worked or not.

The key in this experimental phase is having a regular cadence, aligning with all stakeholders involved, and moving rapidly.


This process was really a team effort – it requires working closely with sales and the rest of the marketing team. Here’s how we generated a 10x increase in our pipeline.

A pipeline just refers to your sales opportunities. All the opportunities in the pipeline are in the stage between a lead and a closed deal. For us, 10x meant we generated 10 times the pipeline versus the year prior.

What I learned from this experience is pretty representative of my marketing philosophy. What’s made me successful in past roles is that I'm not afraid of experimenting rapidly, constantly talking to customers, and looking at data to find the best product-market fit.

Finding a product-market fit is challenging because it’s a moving target and never one-size-fits-all. Product-market fit could mean something different for one segment versus another.

For example, before I started, we had really strong product-market fit with 3PL, which has very different needs than an Amazon or Walmart. That evolution meant we had to make some product adjustments. It was important to know before changing our product that we shouldn’t spend a ton of marketing and sales dollars to go after a segment that doesn’t have product-market fit.

Another central part of our success was aligning KPIs with sales. At project44, we’re really focused on revenue and the pipeline. Marketing qualified leads (MQLs), which are prospects deemed likely to become customers by the marketing team, are important to keep in mind. But we measure ourselves strictly on opportunities that we generate in the pipeline.

I think our pipeline and revenue focus is important because it aligns marketing with sales. It removes the tension of sales saying that the leads marketing sends over are crap, or of marketing complaining that sales isn’t closing any deals they sent over. I saw not only less tension but much better results.

Next, you need to talk to customers to do market research. If you’re not the person responsible for that, at least think about the customer when you’re in a meeting making a decision. You don’t want to make a decision based on opinions. Within the team, you want to pull the customer’s voice into the organization and use as much customer insight as you can.

Finally, do things that don’t compound. As an early stage startup, you should do things that don’t scale. I think that’s okay. You learn a lot from doing that. Eventually, as you learn more and more, you’ll be able to scale a lot of those programs. I believe Paul Graham from Y Combinator is a big proponent of that as well.

Doing things that don’t compound is different. Everything you do should contribute to future success and build toward the future.

Understanding the market, talking to customers, and experimenting all take a lot of work, but these steps lay the foundation for your future success.