The Outbound Sales Stack: The Unsolved Challenges (Part II)

Manav Shah

2 September 2022

The Outbound Stack we explored in Part 1 is evolving and evolving fast. Globally businesses spend over $2 trillion on Sales & Marketing activities and use over 25 to 40 different tools on average, yet struggle to hit their quotes month over month.

In this blog, we will explore, despite this SalesTech landscape crowded with over 1000s of tools, why do teams still struggle to run efficient outbound GTM campaigns.

The broader reason is that teams do not have the right systems, processes, and team checks. Across most B2B organizations, the early focus is always on the product. But one thing that has been a recurring theme that most organizations miss out on is that GTM can be a wedge too. (Take a look at Zoominfo.)

In red ocean markets, with multiple tools at feature parity, you would still see some players stand out. (Eg. Take a look at Sales Engagement; Outreach somewhat just dominates the rest)

GTM teams need to have the best practices, systems, and playbooks set in stone on day one because any later and it becomes increasingly difficult to solve it.

But we will cover that in a later blog. In this one, let’s explore some of the yet unsolved challenges in the world of Outbound Sales Tooling.

Learning & Development

Most AEs/ SDRs take months, if not quarters, to ramp up. Get to a state where they can independently run with leads and convert them to opportunities and closures.

Coupled with the fact that SDRs have an average tenure of < 1.5 years. The RoI for the GTM team is slim at best.

Sales motions are complicated. Each organization has a different process. A different set of tools. And in most cases, no well-defined playbooks for a new sales executive to learn from.

This results in both slow ramp-up time and, more importantly, lost business opportunity on leads that could have been potentially converted.

Companies like Twilio do a great job at this. They have a buddy system and a set of great learning tools and systems set up internally to prevent this. They are able to ramp up their Outbound SDRs in < 1 month. Mega.

Engaging with established agencies like The Bridge GroupRevShoppe, & John Barrows and continuously learning from sources like The SDR Newsletter will help address these challenges.

CRM/ Data Hygiene

It goes without saying how important a CRM is within a GTM function. Everything from revenue projections to sales compensation runs on the data inputted into the CRM. But the challenge is that this data is either incomplete or inaccurate.

The challenge lies both with the system and the people operating it.

Sales teams struggle to input accurate data across the ten different tools. And further, these tools seldom talk to each other to check for these inaccuracies. As a result, the CRM seldom has accurate data to build downstream workflows from.

There have been two approaches here. First, a UI-less solution that connects all your Sales tools to ensure the correct and accurate data sits across all your systems of records and action. is doing some exciting things here.

Second is the approach taken by Scratchpad and Dooly, where the abstract is a layer of ease on top of your CRM. Instead of working with a clunky tool that takes additional friction, they give smart UI layers on top to operate.

Time will tell how this problem gets solved, but everyone agrees that this remains one of the top unsolved challenges for Sales Leaders.


Tools like Zoominfo, Apollo, LeadIQ, etc., do a mega job at providing the data. Tools like Outreach, Lemlist, Salesloft, etc., further provide the tools to reach out at scale. Combined with the growing penetration of these solutions, potential buyers are now bombarded with sequences from hundreds of businesses. Diluting the entire motion.

What we need now is an anti-automation sales motion. Where a company can reach out to the right buyer at the right time with the right message and still manage to stand out from the scores of other potential buyers reaching out.

Tools like Gated are making a move in this direction by bringing an element of charity (really interesting), and Lavender, with their better cold email writing assistant, are some interesting companies solving this challenge.

Sales Intelligence & Intent in a cookie-less world

Many current Sales Intelligence & Intent data provided by the giants of this space comes from third-party cookies deployed across hundreds of websites. But with the world now more focused on privacy than ever before, it’ll be interesting to see how this plays out.

Likes of Apple have already stopped the use of third-party cookies. Cyber Security players like Citrix provide their browser with such functionalities. How will companies like ZoominfoBambora, and 6Sense continue to power intelligence & intent data will be interesting to see

Collaboration across Sales & Marketing

Sales and Marketing have always been two separate functions in a GTM motion. Both have the same objective: build more pipeline and generate more revenue.

Yet, we seldom see them work together, reaching out with the same messaging, targeting the same accounts and leads, and providing the support to win more deals.

Zoominfo and 6Sense are making significant strides to solve just this.

Zoominfo’s Aircover is the one that comes to mind. What it does is it allows SDRs/ AEs to pick the companies they’re planning to engage with to be relayed to the Marketing team, and with a single click of a button, marketing teams can start an SEM, Social Media, and Display campaign on the same accounts. While the outbound team continues their sequences. A mega offering.

With the thousands of tools and billions of spending, a lot remains unsolved and unanswered in the world of outbound tooling. If you are a founder building in this space, trying to solve some of these challenges, and our thoughts at Together have resonated with you, please do reach out to us.

In the next part of the SalesTech tooling, we will look at some companies taking this space by storm. So stay tuned.

– Manav Shah