Outbound Strategy for Inbound Teams

How to start self-sourcing more pipeline.

Sales really hasn’t changed much

I wrote last week’s newsletter while in the air to San Francisco. This week I’m on the way to Boston. While I don’t have as much personal history with Boston as I do with San Francisco, Boston does have a special place in my heart.

The first business trip of my life was to Boston for a startup I founded in college. My cofounder and I, both in our early 20s, thought we should save money by not getting a hotel room on the last night. The idea was to stay out late and get an early flight home—all we had to do was figure out a way to kill a few hours after everything closed. As it turned out, wondering around Boston for a couple hours at 3am wasn’t as much fun as we thought it would be. I did, however, get to see a wharf rat the size of a cat before miserably piling into a taxi for a 7am flight home. I don’t know if that was worth the $150 we saved. Big rat, though.

Boston’s the latest stop on a tour I’ve been doing since December with the goal of talking to as many sales leaders as possible about their goals for the year and how they plan to achieve them. Nearly everyone, it seems, has a plan to drive more pipeline contribution from outbound this year.

These conversations have reminded me of this quote attributed to Picasso:

When art critics get together they talk about Form and Structure and Meaning. When artists get together they talk about where you can buy cheap turpentine.

– Pablo Picasso

I’m beginning to think this applies to sales leaders as well. Maybe something like this:

When LinkedIn posters get together they talk about 17-step AI playbooks. When sales leaders get together they talk about how to get 22 year olds from Chico State to pick up the phone.

— me, I guess

The leaders talking about this are primarily at organizations that have scaled with a pipeline built on an 80/20 inbound/outbound mix. There seems to be a perpetual desire to get to 60/40 or even 50/50.

Let’s look at what’s driving this and what to do if you decide it’s time to invest in outbound yourself.

Why would anyone want to do outbound?

At first, I chalked these outbound plans up to the idea that sales leaders believe outbound is the sales equivalent of getting your kids to eat their vegetables. Inbounds are junk food—easy calories that are bad for your long-term health. Outbound is the leafy greens that don’t taste as good, but keep reps healthy and sharp.

Maybe, but those supposed benefits come at a steep cost. All you have to do is take one glance at LinkedIn to hear that outbound has never been harder—reply rates are low, connect rates are low, and the wall of noise hitting buyers is at an all-time high thanks to AI-driven spam cannons.

In short, outbound is a slog. Why not just double down on inbound if it’s been working?

The answer: declining demand generation efficiency. These folks have done the math and the numbers are clear. They’re pumping more spend into marketing channels for the same amount (or in some cases, less) pipeline.

There are two likely reasons for this: 1) company stage and 2) macro trends.

It just costs more to acquire customers as you get bigger

Some of this shift may be a natural result of company stage. Most of the sales leaders I talk to range from Series B to pre-IPO. If you look at the CAC payback numbers from High Alpha’s 2024 SaaS Benchmarks Report, there’s a big shift to higher CAC payback after $5MM ARR and another shift upwards at $50MM. While this might be the result of better finance practices (i.e. actually calculating CAC payback correctly), it does stand to reason that there are points at which the “easy” growth channels get exhausted and it’s time for a new kind of investment.

Acquiring customers gets more expensive as companies mature (per HighAlpha)

The increase in CAC payback here is a natural consequence of demand gen channel saturation and starting to layer in outbound. Like voice changes and acne, it’s just a natural part of growing up.

That might not be all of it, however. There may also be some macro factors at play here as well.

Driving B2B inbound is getting harder

Broadly speaking, the data on paid demand generation for B2B SaaS does indicate that SEM has gotten more expensive, as have B2B social ads (mostly LinkedIn). And don’t get me started on display (which hasn’t really been about demand gen in a long time).

At the same time, tried and true B2B SEO strategy has started to crash and burn in the face of Google algorithm changes and AI chatbots. The days of writing 1,000 blog posts about tangential topics, parlaying that into high domain authority and then converting the long tail of traffic into inbounds are mostly over. Guess what? Now we have LLMO (Large Language Model Optimization) that may require entirely new approaches.

Overall, there are some compelling reasons why it might be time to at least have outbound as an insurance policy. It’s up to you to decide whether a focus on driving more outbound pipeline is the right thing for your org. However, once you’ve made that call, I do have some advice.

So you’ve decided to “do outbound”

This meme just means I’m old, I think

Outbound isn’t just a switch you flip. It takes commitment because it’s a significant strategic shift that requires new data models, new strategy, new measurement and—often—new people.

Before I get into the details, let me make one simplifying assumption. For our purposes I’m talking about using existing rep headcount and asking them to self-source new pipeline—not rolling out a new BDR function. This is often the starting point for teams that want to start generating more outbound pipeline.

It’s attractive because it theoretically doesn’t add to CAC since you’re already paying for the headcount. But at no point should you think that means it’s easy or has no opportunity cost. Reps will have to split time between responding to inbounds, running sales cycles, and outbounding. That’s a lot of plates to spin. I’m assuming if you’re doing this, it’s because you believe there’s meaningful slack in your reps’ days that can be taken up with outbound. If there’s not, you better believe you’ll drop some plates.

Ok, now let’s discuss.

Data Models

B2B outbound should be built around an accounts and contacts model. Yes, people make the final decision on a purchase, but your customer is the account itself. Most inbound-led organizations tend to organize their motion around leads.¹ That lead-based motion usually looks like this:

1. A person fills out a form.

2. Marketing automation creates that person as a lead in Salesforce. (If you’re lucky, your lead routing logic will try to match that lead to an account using a non-standard field.)

3. The lead gets round-robined to a rep.

4. The rep talks to the lead. If there’s interest, they might convert the lead to an account, a contact and an opportunity and work it from there. If there’s not an opportunity right now, the lead just kinda sits there forever.

The result is fragmentation. People are stored as both leads and contacts in your CRM, and they’re not always associated with accounts. Multiple reps can end up working the same account. Leads that don’t respond immediately languish without follow up. Crucial information about account-level interest gets lost in a sea of people-level data.

If you attempt to go outbound with a model like this, sadness awaits. For example, you could have 5 people who’ve inbounded from Acme over the years but if no one ever created an Acme account, you’d have no way to assign a rep to outbound to Acme. Not great!

You can try to put bandaids on some of these things with ever-increasing lead routing complexity, but the real solution is to move to a contacts and accounts model before you get serious about outbound.

Strategy

I’m going to set aside AI spam cannons for a moment. Thoughtful, effective outbound has a fundamental resource constraint imposed by your quota capacity and time. You can’t reach every account in your TAM with high-quality outreach. That means you have to make tradeoffs to answer the following questions:

1. Which accounts do I go after?

2. How do I organize my team to go after them?

I was lucky enough to be in a Pavilion CEO session with Dave Kellogg recently where he described ABM as “choosing your customers” instead of having your customers choose you. Not all outbound motions are technically ABM, but I strongly believe all outbound motions should be account-based. It really is about about choosing your customer.

Once you’ve built your account-based data model, you need to build a strong sense of which accounts to spend time on in the first place. This effectively means understanding and operationalizing your ICP.

Many companies that try to start “doing outbound” don’t give their reps enough support here. If you hand a rep 1,000 accounts and tell them to figure it out, your reps will either a) not do outbound at all or b) spend all their working hours trying to prioritize.

I can’t stress this enough: RevOps should qualify, classify and prioritize accounts based on as many ICP attributes as possible before ever allocating them to reps.

Going outbound doesn’t mean you need to organize your team around traditional geographic territories. In fact, if you’re trying to get reps who have mostly handled inbounds to start outbounding more, that wouldn’t make sense at all. After all, you’re likely dealing with an inside sales team that’s used to round-robin assignment.

I highly recommend you adopt a dynamic books model where you can start distributing outbound target accounts alongside inbounds. The dynamic books model offers several benefits: you can start by allocating a small number of high-quality outbound target accounts evenly across reps, you can hold reps accountable for covering those accounts, and you can implement a retrieval model to take the accounts away if they don’t.

One beauty of this approach is it allows for experimentation. You can take a subset of your CRM that’s already reasonably account-based (say past customers and opps) and then prioritize and assign that to start with. That way you can test the efficacy of outbound approaches without completely overhauling your CRM and your processes.

Measurement

Inbound KPIs for sales focus on response time and conversion rates to opportunity. Outbound requires a different way of thinking about measurement. I could rehash that here, but I think it’s best to point you to the 3 Outbound Metrics CROs Need.

People

It’s difficult to take a team that’s used to making their number with inbound and suddenly turn those same people into outbound masters. Here are a few things I suggest you consider:

1. Incentives - Does your comp plan incentivize outbound? If you want to change behavior to drive a new strategy, you need to change incentives. One way to do that is to pay directly for self-source opportunity creation or pay different rates for self-sourced deals.

2. Systems - Make sure reps have the systems they need to actually do the work, including a sales engagement platform and, potentially, a dialer (e.g. Orum).

3. Targets - Equip reps with a highly-targeted pre-researched lists of accounts. And don’t give them so many that they get overwhelmed.

4. Enablement - Make sure your reps truly know your ICP and persona challenges so they can think on their feet. Combine that with well-practiced talk tracks and objection handling. A 30-second cold pitch is very different from a 30-minute discovery with a warm lead.

5. Accountability - Reps need to understand they’re responsible for engaging their book of accounts. Activity levels, account coverage and multi-threading should be regular features of weekly conversations with the line manager. Publish metrics for all to see. In a past life, I found it was most effective to aggregate some of these metrics up to the team level and have teams compete with each other. It’s easy to justify not making calls if you’re doing it to yourself, but harder if you’re hurting your team.

6. Celebration - Highlight the reps and teams that are producing the most self-sourced pipeline. Publicly share great cold calls. Celebrate self-sourced wins loudly.

Finally, if you’re serious about transforming your inbound-heavy team to one that can self-source pipeline, know that not every one of your reps is going to make the transition. Be prepared for some hard conversations.

Wrapping up

While there are plenty of good reasons to increase outbound contribution to pipeline, don’t do it just because you think it’s “good for you.” Make sure you’re committed to the process because it won’t be easy. However, if you pull it off, you’ll find you’re likely to have a larger, more resilient, more predictable pipeline on the other side. Godspeed.

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1. I’m speaking in Salesforce terms here. However, Hubspot allows you to shoot yourself in the foot now too.