Awareness > Interest > Understanding > …. Pipeline? - The Truth About Outbound

Here’s a loaded question that's hiding in plain sight as a silly question: what exactly does sales do? Bring in the money of course! However, let’s drill into this seemingly rhetorical question and reframe it to be a little more specific: Is it sales’ job to drive interest in a company’s product and manage deals to close? Or is driving interest a job for what most people would call ‘marketing’?

In truth, the answer depends on a lot of variables and you can find organizations that task sales organizations with much more responsibility to drive interest than marketing as well as companies that are far more invested in marketing organizations to drive interest and overall GTM efforts than sales. While either of the extreme examples above can be right for any given number of reasons, typically most companies generally task marketing with driving interest (i.e. website visits, leads, etc.) and task sales with managing and closing all the deals (opportunities in your CRM) that come from leads generated by marketing.?

Here’s the problem: conventional wisdom or an inherent bias for sales or marketing led efforts often lead to the oversimplification, mischaracterization and under optimization of outbound motions. Outbound isn’t dead .. but it needs to be reevaluated in order for it to be successful.?

The Omega AE: Outbound Selling at The Seed Stage

Years ago I was the first AE at a Seed stage company with $100Ks in revenue that needed to close enough customers to clear $1M and land their Series A. I was the entire GTM org at the time and while we had some strong founder and investor driven inbound we didn’t have any marketing or lead generation. Thus, we did a lot of bespoke outbound motions targeting good fit companies and the key leaders that made up “v1” of our ideal customer profile. This company’s product was an entirely new category with a concept that wasn’t known or accepted yet within our target market and we needed to offer clarity on what we were doing before expecting productive discovery discussions.?

Using the skills I’d built up over the years and with help from the founding executives, we managed to land a great number of meetings with Director, VP and C-Level contacts across various segments where our product could fit and provide value. These conversations were very valuable and early on we learned some hard and painful lessons. However, in a very short amount of time, we got pretty damn good at explaining what we did, the value it could provide and getting key decision makers interested and excited about the possibilities.?

However - as expected -? not all of these good introductory meetings turned into deals right away. While we managed to find prospects with timely priorities and motivations that closed quickly, many other deals never materialized. However, a great many of these companies came back to us several months later via inbound forms and other channels, ready to engage and became the qualified deals that got us over the $1M revenue mark and led to our Series A.

This was a great success, only diminished by snarky comments by an executive claiming how all of the deals were “inbound” and not sourced by sales. This was categorically false - much of the deals were meetings booked from cold outreach that later, after their particular journey, came back to engage with us. Early marketing and product led efforts absolutely helped - it was a synergistic effort and win for the whole GTM team to celebrate, not a wedge to drive between team members.

Going Up Market with “Champagne Problems”

Fast forward several years, I found myself at Asana selling another new emerging product from a new category. At this time, there was a tremendous amount of traction via self serve and low touch sales assistance thanks to the product backed by strong founders and a truly fantastic marketing effort that leveraged a great product and established Asana as the early leader in the work tracking category. The only challenge was that the vast majority of the fast growing revenue at the company came from the SMB segment (typically under 500 employee companies, often well under 100) with very little traction in the Mid Market and Enterprise segments.?

Asana had a “champagne problem” (well before it was a Taylor Swift song) - it was growing rapidly thanks to strong marketing and product led growth (as well as a small, strong and spartan sales team) - yet to reach its potential it needed to accelerate and grow revenue from Mid Market and Enterprise companies that had higher long term upside than SMB companies. As one of the first of the initial handful of sales people hired, I knew this would be a hard problem to tackle, especially when Asana was winning big and growing fast, even without a lot of larger (in terms of company headcount) paid customers. There was also resistance to change due to the very real risk of interrupting or harming customers on the right journey that were driving strong revenue growth via self-serve and a minimal sales assistance.?

Eventually after some time in my tenure, I was tasked with being the very first person to do any true outbound at Asana, focusing only on the Mid Market and Enterprise segments and not working on any SMB accounts (a segment that was already wildly successful thanks to groundwork laid by the earliest leaders at Asana.) Just as I had done before as a seed stage AE years back, I curated a target list of strong fit companies and a list of target contacts with titles and functions that could get immediate value from Asana. I executed experiments, proved out some concepts, built a plan and hired our first outbound sellers.

As expected, the results were pretty good: after some epic and hilarious failures in the first month, we? ended up landing a lot of meetings with good contacts and getting traction with bigger companies. Just as I had previously experienced, there were some quick wins (new paid logos) but often our best meetings were with senior leaders that wanted to educate themselves and understand the work tracking category, why Asana was the leader in the space and how it could align with their current and future priorities.?

Months later, many of these prospects came back to us via inbound channels or in some cases even purchased via self-serve (i.e. a Director/VP puts $10K on a credit card for their team of 10-15 people.) In these scenarios, tracking and the attribution of the different stops on the customer journey was a challenge. For example, if a VP we had a meeting with later tasked a direct report with using or buying Asana 2-6 months after we met them, some manual leg work to connect the dots was needed to connect it to our efforts.? Asana Sales Operations - a team that was the source of truth and conscience for all things GTM at Asana - helped us to iron out the data and process. Just as I had experienced before, outbound efforts worked, but often did not turn into qualified pipeline deals right away. Customers would be introduced to Asana by outbound sales and then would engage with various campaigns and content from marketing or perhaps even experiment with the free product before coming back into the mix thanks to multiple touches across sales, marketing and product.?

Eventually the process became predictable enough to create the Enterprise Inside Sales Team that would prospect and close smaller deals to set up bigger, larger opportunities with shared services and executives by our most senior Enterprise sellers. While not unprecedented (the role had been used at Box, New Relic and others) it was a unique and somewhat disruptive to have this role and org structure to match the optimal customer journey at Asana. However, in the end, Asana went up market and sold its way into some of the world’s biggest companies with huge deals on their way to IPO and beyond. These days, the company is increasingly focused succeeding within the Enterprise segment.

The Truth About Outbound

While the experiences I’ve shared are hardly uncommon, there’s a part of it all that’s potentially disruptive to how we think about outbound and the role of sales and marketing. Successful outbound motions and well executed introductory meetings do not always equate to qualified pipeline deals, especially if the customer is early in their journey and the concepts, values and category of the product are new to the target markets. This is why all over tech there are stories in every sales org of really great introductory meetings with executives that take months (years?) to materialize into qualified deals in a company’s forecast - assuming they materialize at all.?

This raises a big question:

Is this outbound work truly sales? Is it marketing? Something in-between? Or something altogether unique within a GTM organization's plan?

Outbound by humans or machines/AI is useful because it allows you to directly and explicitly target prospects with what is ideally the right message at the right time vs. large scale marketing campaigns or brand work. As I’ve discussed publicly before, with the dawn of AI driven automation tools, there are both tremendous opportunities and risks to balance for companies looking to utilize outbound GTM motions.?

The truth is that outbound success does not always equate to short term qualified sales deals/pipeline for a given month/quarter/year. Moreover, successful outbound (opens, replies, intro meetings) will often drive strong inbound leads across various channels in the long term, often many months after outbound efforts kicked off a prospect’s customer journey.

Is outbound effective? It absolutely can be. However, it must be managed as a connected process with other touch points on the ideal customer journey vs. two mutually exclusive lead source categories.

It is also critical to realize that outbound that isn't wisely designed and successful has a very high cost: irritated prospects that get a poor experience, tune out, delete or unsubscribe.

This is hard … but very, very necessary

RevOps teams all know that multi-touch attribution for leads is really hard, but it is now mission critical if GTM structures and plans are to be optimized for the best results. If company planning turns into a lame episode of ‘Game of Thrones’ where different teams are vying for credit and easy wins vs. shared goals and targets, then toxicity (and often outright failure) will inevitably follow. Company leaders need to do the work and be intentional with how they structure their roles, targets and incentives that are related to 'outbound' motions. This is especially true in regards to how senior leaders incentivize leaders that they directly manage.

There are some critical questions that leaders need to ask themselves before proceeding with outbound:

• When should an outbound role - whether human or machine - exist within Go-To-Market teams?
• Should organizations consider replacing SDRs/BDRs with Product Advocates or Customer Education Agents, whether AI-driven or human?
• What should be the role of Outbound Rep + AE outbound activities in the overall pipeline generation strategy, plans, and targets? Is there a scenario where they should not be included at all?
• Should all or some outbound type roles or products be under the ownership of sales or marketing departments?
• What role does the outbound rep or “AI SDR/BDR” play in the optimal customer journey? (if at all)

Each scenario demands unique considerations and will yield different best practices. It's likely that these pivotal questions are being overlooked, underestimated, or oversimplified by leaders who are eager to go “outbound” to juice their pipeline and hit growth targets.

In the end, managing outbound directly points back to optimizing for the customer journey. Companies need to refresh their perspectives on what the precise roles of sales and marketing are within their GTM organization and put together operational plans that will actually succeed today and beyond with the buyers everyone is trying to connect with. If one finds themselves doing the same things as everyone else and using tired cliches from “Boiler Room”, “The Wolf of Wall Street” or “Mad Men” when discussing GTM best practices and plans, it may be time to for a hard reboot.