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Many startups don’t have a sales rep so they invest in content marketing and other means to generate inbound sales. 

Outbound sales is almost never considered as it “can be intrusive, so many people are turned off by it”, according to Bastiaan Janmaat, ex-CEO of DataFox & VP of Product Management at Oracle, on the SaaStock stage.

However, when done right, you can reap many benefits from outbound sales.

Watch now:

People who are experiencing a pain, search for a solution, find you and contact you. You then together explore whether there is a fit between your solution and their pain.

But many other people who may also be a good fit for your solution, just haven’t heard about you. And so, you have to find them, and explore whether they have a pain that’s severe enough for there to be a good fit.

How do you do that?

There are four things you need to get right with your outbound sales strategy:

  1. Focus on the right companies to go after;
  2. Build a relationship by taking a personalised approach;
  3. Incentivise your reps to do the right things that you want them to do;
  4. Support your sales team with collateral and marketing efforts to educate your future customers.


Find out how to build your outbound sales strategy in 60 days. Watch the full video with step-by-step guidance from Bastiaan, on our YouTube channel. You can also read the full transcript of this video below.👇

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Bastiaan Janmaat:

I wish I could’ve picked my entrance music, but that was default. My name is Bastiaan. Thank you all for spending some time here today. I’m the CEO of DataFox, a company in San Francisco. I’m a first-time CEO, so there’s absolutely no evidence that any of this is going to work more than once. But we’ve tried a couple of things in building our outbound sales strategy, and some things have worked. Others haven’t, and I’ll present that to you today. Actually, one of the bigger mistakes we’ve made or that I’ve made is in building our outbound sales strategy too late frankly. Like many startups, when it was just myself and three co-founders, we invested in content marketing. We didn’t have a sales rep. We were doing a bit of sales, but we invested a lot in content marketing and other means to actually generate inbound sales.

It was a bit of of a double-edged sword. It worked well enough that there wasn’t that much urgency to really go outbound, but not so well that we didn’t need any outbound sales. I first really realized that at a board meeting where I was presenting our forecast, our sales forecast and the board members were grilling me on, “How sure are you that you’re going to hit this growth trajectory?” And I’m like, “Well, I’m not that sure actually.” You’re beholden to inbound at the time, and that’s when I realized we needed to make up for lost time and really take more control of our pipeline, and do that by investing in outbound. We did that very quickly. We built an outbound sales team, and that’s what I’m going to walk you through today.

Before I hop in, let’s do a really quick poll. Who here runs or works at a company that has a sales team? Okay. That’s probably about 70% of the room. Now, keep your hands up. Now, keep your hands up if you’ve got dedicated outbound sales reps. Wow. That’s a pretty high percentage. Eyeballing that, probably about 80% of the companies with sales teams have dedicated outbound reps. That’s pretty cool. Everyone’s talking about account-based marketing, account-based sales, account-based prospecting. It’s really kind of funny because all it really means is focusing your marketing and sales efforts on specific companies. That’s been happening in enterprise sales for 100 years, but people are adopting it now in SMB and mid-market because we’ve seen that it’s hard to break into accounts without taking an approach like this. So it’s really just new terminology, but there are tactics being employed. They’ve been around for a long time.

Anyways, without further ado, let me hop in here. Some trouble with the clicker here, guys. Here we go. Outbound sales. One of the reasons I mentioned we hadn’t adopted it was that inbound was working well enough. But another reason was that I had a somewhat negative impression of outbound sales from being on the receiving end of phone calls and emails. Outbound sales, it can be intrusive, so a lot of people are turned off by it. But it’s absolutely necessary and there are many benefits to it. If you think about the folks who are finding you coming your way, those are people who are experiencing a pain and they hear about your solution, and then they contact you, and then you together explore whether there’s a fit between your solution and the pain that they have.

But there are a lot of other people out there who are a good fit for your solution too, but who haven’t heard about you. And so, you got to go out and find them and then explore whether they have a pain that’s severe enough for there to be a fit there. It actually was coined by Mark Roberge from HubSpot. Now obviously, a big problem with outbound sales nowadays is the problem of scorched earth. There are reps that are fresh out of college and you arm them with an email drip campaign tool and the ability to go get 10,000 email addresses somewhere. Suddenly they’re not just your outbound sales rep, they’re your marketing team too. I’m sure everybody in this room gets at least an email a day where you’re like, “Geez, come on. Are you serious?” They left the first name placeholder or it’s fake personalized, but really not personalized at all.

That’s not just a bad email and a missed opportunity, it damages your brand and it’s also potentially damaging a future inbound opportunity. So there’s an agency problem here, right? We learned that in economics 101 or business 101, that the incentives aren’t aligned there. That rep is just trying to get their activity volume up and generate some leads. But to you, as someone running the sales team or running marketing, or running the business, there’s a lot of damage that can get done there. The problem is really twofold. What I just described was more of a spam problem, right? It reflects badly on your company. But the other problem is, they’re just wasting arrows on companies that probably aren’t the right fit in the first place. So there are two things we need to get right with our outbound sales strategy, focus on the right companies, and then approach them in a way that reflects well on you as a business.

These are the four steps that we took in our outbound strategy. And like I said, maybe it’s just slightly different terminology for things that good sales teams have been doing for a long time. Pick the right companies to go after, build a relationship by taking a personalized approach, incentivize your reps to do the right things that you want them to do, and then support your sales team with collateral and marketing efforts to educate your future customers. Now nowadays known as account-based marketing. Let’s start with building an account list.

I’ve found that people way overthink this sometimes. You don’t need to hire a data scientist to figure out who the right accounts are for you to go after. Set a goal. It depends on obviously many things, the nature of your sales cycle and your price points. But maybe you’re focusing on 100 accounts or 300 accounts per rep at a time, pick companies in the right industry, with the right head count, in the right geography. Then we did a couple of simple things to then narrow that list down. Grab your account executive when they come off a call and be like, “Hey, what are the things that at the beginning of your call with that prospect, if the prospect had said those things about themselves, you would have been excited about them being a good fit?” You might hear things like, “Well, if they have a lot of designers on their team, it’s a good fit for our product.” Or, “Gee, if they sponsor a lot of conferences, I’ve seen that be a good signal around that being a good prospect for us.” Or, “Companies that have at least three offices, much higher propensity to buy.”

Again, you don’t need a data scientist. Just talk to your sales team. What are their heuristics that they’ve been using? Now, number of designers, number of offices, conferences sponsored. That’s probably not available through data.com or some other database, so we use Upwork. Used to be called oDesk. Use some contractors, give them clear instructions. They can Google-search and LinkedIn-search their way to building out that spreadsheet. That’s often a great way to start. You have your countless now. Now, who do you actually reach out to at those accounts? You’ll have a sense already of which roles and titles you’re looking for. Two things we learned. Number one, it requires more than one outreach, obviously, per contact to get a meeting set. It also requires more than one contact per company to get a meeting set, and I’ll talk a bit more about personalization in a second. But for us, a rule of thumb is, if we’ve decided a company is a good fit, find at least five contacts, let at least half of them be senior titles. Just a rough rule of thumb.

Interesting stat from, this is a three-month sample. Lower-level folks sometimes don’t show up, even if you’ve reminded them. Senior folks, in this sample, we had 0% no-shows. It could be a variety of reasons for that. Maybe they’re thinking more strategically, and so if they’ve agreed to take that call with you, then you know it’s a high priority for them. Junior folks, maybe they took the call, but aren’t that bought in yet. It just speaks to the importance of going in high early. As a side note, how do you reduce the number of no-shows? Obviously, send a reminder before the meeting. A lot of reps don’t do that. It helps enormously. Number two, ask for the prospect cellphone number and put that in the invite. It does two things. First of all, you just get a natural inclination for people to be more bought into following through on the meeting that they’ve agreed to because they know that they gave you their cellphone number. It might be subconscious.

Secondly, if they miss the meeting for whatever reason, you can reach them directly. You don’t have to go through a switchboard or send them an email that they might miss, causing you to miss the meeting. Number two, in your face personalization, also known as just do your homework and build a relationship. What is not personalization? Congrats on your funding round is not personalization. Let me tell you a quick story. We used to send congrats-on-your-fundraising emails. And then in July last year, in July 22nd, I’ll never forget it because it was a black day in my inbox. We announced our funding round and I got 200 phone calls and emails of people selling us recruiting services and real estate, and software, all kinds of things. That was the worst day in 2015 to try and sell me something. Obviously, because customers are also reaching out based on that press release, and recruits, and potential investors in future rounds. So literally the worst day of the year to reach out.

It all turned into static. I probably didn’t respond to any of those emails, even if some of them may have been a good fit. Think about that for a second, right? We announced it in July. No company announces their funding around the day that paperwork is signed or the cash hits the bank account, you prepare your announcement, and you align it to a product launch or something. We raised our money in May, and then started spending it. Hired a bunch of people, got an applicant tracking system, moved into a bigger office, bought healthcare, bought insurance, all this stuff. Bought marketing software, and then we announced it. If people had just reached out earlier, they would have been in a great position. Or reach out later when you aren’t drowned out by everybody else.

What is in-your-face personalization? Basically, it’s doing enough homework that when your prospect reads the email, they can’t avoid going, “Wow. They did their homework.” Is a rough rule of thumb, but it really has two benefits. First of all, in doing your homework, you’ve convinced yourself that this is indeed the right prospect, and it’s worth your time, and it’s worth their time. Secondly, they read it and it makes an impact. I’m happy to post this screenshot on Twitter, but it’s one template where short intro, and then three things about the prospect’s company that lead us to believe that they might need our product or our services. Then a more standard template paragraph describing what we actually do. It generates responses like, “Hi, Brooks. That was one of the most compelling sales emails I’ve ever read. Can we schedule a demo tomorrow afternoon?”

But the key thing that I’d like you to take away here is that we’re not trying to trick them. It’s not like, “Oh, what cheeky thing,” or conniving thing, “can we come up with to get this person to respond?” We just genuinely did our homework and think there’s a fit there. Obviously, this got us more responses. Let’s call it about a 3X improvement in response rate. But why is the number of meetings set? Why does that go up by less than 3X? Is that bad? It’s actually not bad. It just means that there are some people who responded who didn’t want a meeting. But who are those people? Those are people saying, “No, thanks.” No thanks is a great response, for two reasons. First of all, now our rep won’t continue doing a bunch of homework on this person. So opportunity cost of that time, time saved.

Secondly, you often get some intel out of it. This prospect had just purchased LinkedIn Sales Navigator. Great. In a follow-up, they might be able to share with us when that contract comes up, or how they’re thinking about their tech stack, exchange an email or two, and then put that on your calendar. That is golden information around when to reach out later on. So getting a no thanks is hugely valuable. So what do we look for if we’re not looking for funding rounds? We’re looking for company milestones. It depends on what you’re selling again, but any evidence of the company’s growth or spending on marketing. By the way, I just posted this screenshot to the top of my Twitter feed, which is in bottom left-hand corner. So if you can’t see it from the back, you can can grab it there, but there are about 60 different signals that we look for depending on what we’re selling and to whom.

And we have this rule, no outreach without research. You’ve gathered that by now, and no followup without reason. Which means, it is absolutely not allowed to send an email to a prospect from our company that says, “Checking in, did you see my email below?” That’s just excruciating. I hate being on the receiving end, and it’s almost like someone writing something onto your to-do list. Right? You’re super busy. Many of you use your inbox as a to-do list, and someone just wrote their thing at the top. It wasn’t a priority. It wasn’t a fit, and then the next day they write it at the top again. We feel that we can’t do that without earning the right to do that. And you do that by either doing more homework and sharing that, or by sharing some information, or a white paper, or a link to a blog post that might be helpful.

Number three, incentives. This is one rep across three months. They had about a thousand phone calls and emails a month. They had about 40 call connects. Obviously, a lot of phone calls lead to voicemails or just couldn’t get through. About, well, no, exactly, this is real data. 20 meetings booked by this outbound rep for his account executives every month. We had a thesis that we weren’t making enough phone calls, and so we tested that. In month four, we had twice as many call connects as the average of the prior three months, up 100%. Led to 35 meetings booked, and that trend has persisted. Two takeaways here. First of all, reps, especially young reps, are not making enough phone calls. Secondly, if you don’t set these very explicit goals for your reps, then you can’t iterate on something that you’re not measuring.

If you look at our dashboards, for those of you who can’t see from the back, this is a screenshot of a couple of things we measure. For this outbound rep, for this BDR, they have to make 30 activities a day. 10 of them need to be calls. There’s actually another metric for call connects. Then we also have a dashboard that shows, how many prospects have received their first email, but who we haven’t called yet? That number is red because it’s way too high, and so he knows that right now he needs to make those phone calls to get that number down. Like I said, if you don’t measure it, you can’t iterate on it.

Account-based marketing. Who here actually knows what account-based marketing is? Very few. It’s a very hot topic in the United States, or in the Silicon valley, especially right now. Basically, it’s marketing initiatives targeted at specific accounts. Think about it as fishing with a spear instead of with a net. A couple of examples of what account-based marketing is and how it’s helpful. When we designate those accounts that our reps are going to go after, before Brooks and his teammates start calling and emailing into accounts, we buy LinkedIn ads, which you can now use to advertise to specific accounts. It’s pretty awesome. You can upload a CSV of company names, URLs, say, “I only want to advertise to people with certain titles at these companies.” It’s incredible.

We do that about 30 days before our sales team starts going outbound. What that causes, even if nobody’s clicking on those ads, we get responses like, “Oh yeah, I’ve heard about you guys. I don’t know where.” So it just puts you more top of mind. It gives some recognition. Makes you look bigger, so very helpful to do that. We usually do this for about 100 tier-one accounts and anywhere between 500 and 1,000 tier-two accounts at a time. Other examples of account-based marketing. Again, traditional salespeople have been doing this forever. But software sales and SMB, mid-market, not as much. We send books to people. We deliver donuts by hand, if they’re in San Francisco. We send t-shirts and sunglasses. Honestly, it’s a little hard to quantify the impact, but it helps build a relationship. It’s not that hard to do, especially sending a t-shirt. People are just advertising your company when they’re going for a run and sitting in their office. So it’s a little hard to quantify, but I found it to be very powerful.

The other thing I do, myself and our head of sales, we host leadership dinners where we invite in a handwritten email, no HTML. We send an email to six to 10 people. Usually decision-makers at accounts we’re prospecting into, and we invite them to a dinner. It’s nothing fancy. It’s at our office on a Tuesday night. We order some tacos or whatever. It’s great conversation with 10 leaders amongst the companies that you’re trying to build relationships with. It’s been super helpful.

That’s it. Like I said, most of you probably look at this or have heard me go through it and you’re like, “Well, no shit. We’ve been doing this for a long time.” But for us, putting it in this order and tying it together was really helpful as we built the strategy. And the results have been measurable, two to three times higher contract size on the outbound deals versus the inbound deals. You’re spear fishing, right? So obviously, you’re going to go after the big ones that are likely to be a good fit. Pipeline velocity due to these ABM initiatives, these dinners, sharing high quality content. And a lot of these deals that we go outbound into, they may not turn into an opportunity right away, but then we see them come inbound later on. Sometimes not even the same person, but someone in their team where they’ve clearly talked about our solution.

Then like I said, your sales team, if you’re going outbound, is an extension of your marketing team. So instead of scorching the earth, use this as an opportunity to build your brand and develop a reputation. For those of you who are looking at this and you’re like, “Oh crap. I mean, some of these things we should probably be implementing,” you’re not alone. We work with companies as big as UPS and young seeds, series-A-backed companies in the Valley and implementing these kinds of methodologies. A lot of our methodology rests on these signals, these milestones that we unearth. That give us the confidence that someone’s a fit, that we can also use in our outreach to show that we did our homework and build a relationship.

I’m going to stop there. Thank you very much for your time. We’d be happy to chat on Twitter or as we roam around the conference. Enjoy the rest of your conference. Then I get to very, very briefly mention to you who’s up next. We have a panel titled Driving Enterprise Hypergrowth Using SaaS Applications. Four founders of some very exciting SaaS businesses. The panel’s moderated by Nicolas Wittenborn whose LinkedIn profile says he’s at Point Nine, but I think he just moved to Insight Partners. A great moderator.

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