The Future of Work for B2B Sales

Table of Contents

The world of sales has gone remote. In order to be competitive, businesses need to have a well oiled outbound sales team. However, the mass adoption of outbound sales automation tools has resulted in flooded inboxes. Getting your “foot in the door” with new buyers is more challenging than ever.

Not that it was easy pre-covid...

Over 126 trillion B2B emails will be sent in 2023 alone (Statista) and "spray and pray", templated emails are proving to be less effective.

To spark conversations with inbox-innundated buyers, sellers need to be more methodical than ever in their prospecting and outbound process. It's no longer enough just to populate a few {{custom fields}} and drop a contact into their "persona's" email sequence.

The quota-crushing sellers tend to be those who have iterated on 1,000's of outreach attempts. These sellers tend to have one thing in common - each has an arsenal of dynamic messaging and outreach tactics, based on relevant info they're able to unearth on target prospects (e.g. firmographic info, news events, intent data, industry-level trends, shared interests, mutual connections, previous traction they/their coworkers have had with an account, social media, etc.).

Here's an (fun to visualize) analogy I've found effective when explaining the problem to my Grandma...

Sales is like baking a cake.

On the extreme end, there are two types of salespeople. Sellers who "spray and pray", and people like Ace of Cake's Duff Goldman. Spray and pray sellers are dumping skittles out of an airplane onto a crowd of sunbathers (painful, right?), and Mr. Goldman just cashed another check, hitting $5m in his bank account.

The difference? Mr. Goldman knows how to bake an unbelievable cake that his customers love. Rather than throwing cheap skittles at unsuspecting strangers, Duff has mastered his craft of meticulously piecing together ingredients into cakes that have won the attention of Oprah and Jay Leno.

The best sellers know where to look to find the ingredients that will enable them to bake the best cake.

Unfortunately, that prospecting process is painfully monotonous, time consuming, and tricky to learn. Similar to how there are very few pastry chefs like Mr. Goldman, only a fraction of sellers have mastered the outbound craft. They make up 20% of the headcount on a sales team, but bring in 80% of a company's revenue.

After grueling years of "cake baking" for sales teams at Oracle and Yelp, Kyle and I launched Autobound to build the technology sellers need to be experts in their craft, just like our friend Mr. Goldman.

Autobound empowers SDRs and AEs to personalize their messaging at scale. A “top notch” prospecting and email-writing process, which might take a seasoned seller 30 minutes to perform, is done instantly with Autobound.

By capturing information on a sales team’s buyer personas and sales process, Autobound empowers reps to engage the hottest prospects with the best message at the right time. Think: Mr. Goldman simultaneously delivering a custom cake for each fan of his at Coachella, right as they get hungry.

The genesis of Autobound’s system is built on what’s been proven to work in the field. Autobound aims to consolidate a time consuming, monotonous, and expensive sales process.

For context, sales teams with deep pockets might use Zoominfo for contact data, Clearbit for enrichment, Bombora for intent data, Outreach/Salesloft for sequencing, LinkedIn Sales Nav for social selling, and Gong for conversation intelligence. The trickiest part of being an effective outbound seller is knowing how to integrate all the important data into an email, and having the tenacity of doing it 100x each day, every day...

Not to mention knowing (guessing) which prospects even makes sense to prioritize in a given sales territory. Most reps start each fiscal year looking a bit like Spongebob...

Even for those reps who do spend the time uncovering the right data before constructing their outreach, they seldom know what situationally relevant messaging they should use (questions they should ask, pain points to dig into, and so on).

For some teams, the problem is far worse - I used to have SDR colleagues who paid $7/month for an auto-clicker to fake phone calls and emails…. At a company with a household name.

Even high performing sales reps regress to sending one-size-fits all, templated emails at a frightening scale. There's no better way to burn a bridge... it's all too easy to tarnish a company's brand, decouple existing relationships, and get a domain blacklisted. Getting hit in the face by skittles hurts (if you don't know what I'm talking about, scroll up).

As a result, sales management has been cracking down on who can create content, which makes the messaging even less malleable to the use case of the prospect-at-hand. Worst of all, this takes away the salesperson’s ability to personalize their message, and iterate on what works best for them. We're firm believers that the outbound process should be extremely buyer-centric, but relationships are a two-way street.

Sacrificing quality for quantity.

When Duff went on the Food Network Challenge, he had to study the judges and bake a cake he knew they'd love (and he did, over 7 hours). If he had the same amount of time, but needed to bake cakes for 1,000 judges, they might not taste quite as good.

Unfortunately for SDRs and AEs, this tug-of-war is all too real.

We're aiming to narrow the gap between personalization and scalability. The future of outbound sales is driven by quality of execution, and no longer requires a total sacrifice of quantity.

By automating an advanced prospecting process across each company in a sales team’s CRM, Autobound's system presents sellers with an intelligently prioritized feed of click-to-send campaigns (prospects matched with contextual email content). Here's what clicking into one looks like:

We built out system to take sellers to the 1-yard line. A user friendly logic-based system enables a team to program custom “if this, say that” sales messaging as they use the platform. The more a sales team send campaigns, updates messaging, and creates new logic based outreach, the more sophisticated and targeted future suggestions become.

From day one, each seller on Autobound has access to our proprietary database of smart sales copy, which is molded to them during onboarding. This smart sales copy is continuously distributed to existing users as new trends and abilities to personalize are learned by our technology.

The result - Autobound’s engine recommends high quality, targeted sales emails based off of salient sales data. Our integrated sales workflow collapses fragmented data on a user’s prospects to create a never ending feed of “suggested campaigns”.

This powerful prospecting process happens in the background for everyone at once. It also gets better with use, similar to how TikTok presents a user with a feed of extremely relevant content based on learned preferences.

The ingredients.

Here’s some context on the sources of input data for a suggested campaign:

  • The user’s instance of Salesforce
  • Contact data partners, giving users access to contact information for prospects who match their personas
  • Our data partners, enabling admins to integrate “3rd party triggers” into their sales team’s outreach, including, news events, technologies used, job openings, networks & shared connections
  • Our proprietary database of situationally specific sales messaging (like playing a game of “Mad-Libs”.

To give you a better idea of what the output of Autobound looks like, below are some example excerpts from our suggested campaigns (with associated inputs). See if you can figure out the associated “logic” before scrolling down. The following descriptions of “logic” have been simplified for example’s sake.

Example message: “Wanted to circle back from when Samantha on your team evaluated using our bookkeeping automation system in Q2 of last year. I believe your team went with Quickbooks, how’ve things been with their tool?

Supporting Logic: {{Closed lost opp EQUALS TRUE}} AND {{Competitor Lost To EQUALS QUICKBOOKS}}

Primary Input: records from Salesforce Opportunities


Example message: “Following up from my note in March, trust you’ve been well since. Have you given any thought towards how our system could help you reduce time-to-hire for new SDRs, and enable them to spend more time selling?”

Example logic (SFDC): {{Last Activity Date GREATER THAN 30 DAYS AGO}} AND {{Stage EQUALS QUALIFIED}}

Example logic (AB Persona): {{Persona EQUALSSales Enablement”}}

Primary Input: records from Salesforce Activity Fields & Autobound’s Persona Classification System


Example message: Saw your sales team is set on growth, just read through the open SDR positions on your career page. Are you concerned with how long it’ll take them to properly learn how to prospect through {{CompanyName}}’s Salesforce instance, as well as properly internalize your sales messaging?”

Supporting Logic: {{Technology Used CONTAINSSalesforce, Gmail”}}

Supporting Logic: {{Job Openings CONTAINS “SDR”}} AND {{Count GREATER THAN “3”}}

Primary Input: records from Technologies Used & Job Openings


Example message: Just saw the Techcrunch article on {{CompanyName}}’s $25M Series A round! Huge congrats to you and your team, a16z is a phenomenal firm. With the focus on scaling revenue and growing your sales team, I think Autobound’s sales intelligence platform could be a game changer”

Supporting Logic: {{Event EQUALSSeries A”}}

Supporting Logic: {{Investing Company IS KNOWN}} AND {{Amount IS KNOWN}}

Referencing Records from Real-Time News Events

Primary Input: Records from news events (Series A to be specific)


We hope you've enjoyed reading. If you're interested in learning more or seeing a demo, you can click here to get in touch with our sales team.

- Daniel

Daniel Wiener

Oracle and USC Alum, Building the ChatGPT for Sales.