In Enterprise Sales, All Opportunities Are Not Created Equal


2020 is continuing to bring change to the world of enterprise sales, we’re starting to see the shift occur from the pure “meetings madness” of the 2000s, to the maturation and saturation of the B2B SDR function in the 2010s, to something new.

What does the newer model look like? Importantly — what does it not look like?

Enterprise Sales Development Isn’t What It Used to Be

Broadly, two things happened:


  1. Buyers got wise to the original mass-email “appropriate person?” tactic that Salesforce popularized. Then, they realized they were being prospected in new ways en masse by entry-level salespeople (“sales development reps”) without anywhere near as much knowledge as the last generation of sales reps had. Collectively, their guard went up even further against receiving cold prospecting calls and messages.
  2. The amount of information available to buyers — without or before they talked to a salesperson — has increased rapidly. Review sites like G2 as well as software companies’ own B2B content marketing efforts have seemingly made freely available all of the necessary information that a buyer would need.


This effect further reduces the need for salespeople to do transactional prospecting: buyers expect them to bring not just facts, but wisdom and knowledge, to the conversation. The proliferation of SaaS as a whole means that the bar to truly stand out for software salespeople is higher than ever.


The Nuances of Lead Generation

All of this has put the marketing, sales development, and lead generation teams on the defensive — especially when it comes to selling complex technology solutions to smart sophisticated people at large established companies.


In short: in years prior, you could reliably send 20,000 emails and schedule 200 meetings. It was never the best idea, but that didn’t stop unsophisticated sales teams from succeeding at selling appealing new software products this way.


But what we missed in all of this was a truth that veteran salespeople have always known: Not all sales opportunities are created equal.


We’ve always known that a trusted customer introduction to a prospect is better than a meeting scheduled from a cold call. Now it’s time to explicitly unpack and teach the nuances of this concept to the sales development and marketing teams of today so that the lead generation strategies they use can mature and adapt to the needs of now.


Quality vs Quantity

In the enterprise, pipeline — not leads — trumps everything.


“If you can close 7-figures with 3 meetings, awesome and if the other person right by them does it in 23 meetings, equally awesome.  Leaders that get caught up in the minutiae are focusing on much of the wrong work.” – Amy Volas, Avenue Talent Partners


Every salesperson intuitively understands that some meetings are just better than others.


In a poor quality meeting, the prospect barely remembers who you are, is taking your call on their hands-free car phone on their way to lunch, is connected vaguely at best to the problem you claim to solve, and really wishes that someday they’ll be in control of the budget.


In an excellent meeting, the prospect already knows the seller via their personal reputation, going in; the seller’s other customers have vouched for the quality of the solution and of the seller’s character. And the buyer not only experiences the same pain point that’s relevant to what’s being sold but is on the buying committee and influences decisions on how budget is allocated.


Good sales development teams understand how to conduct excellent discovery but many are still slinging appointments at whatever cost, no matter how much arm-twisting is required.


The first lesson to the modern enterprise sales lead generator is this:


Remember that people with an abundance mindset and a high-quality product have no need to convince anyone of anything: in sales, all we are doing is helping others discover and realize their problems and the potential solutions. We aren’t persuading or manipulating anyone.


Telling a buyer on a cold call who is trying to get you off the phone that you “guarantee” it’ll be worth their time to take a meeting, when you’ve spoken to them for 120 seconds, constitutes manipulation — at best.


Context Matters

Salespeople have more clues than they think as to where the buyer may be in their journey. For one, the distinction between an outbound-sourced meeting and an inbound-sourced meeting brings a few large differentiators:


  1. When we outbound prospect someone, we introduce new information very early on in the buying process. We need to back off more, have patience, inspire excitement, and act as a guide toward helping someone shift their perspective.


  1. An inbound lead is likely further along in their decision-making process. This is good in the sense that you are already likely on their shortlist (or at least medium list) of potential solutions and means your sales cycle will be shorter. But it also means that you didn’t necessarily handpick this prospect, so they may not be a perfect fit. Additionally, you’re far more likely to be in a competitive situation where you don’t know what other solutions they’re investigating, but you can be sure that they are looking at multiple providers.


If you’re a VP of Sales or Marketing compiling your Sales Cycle and Pipeline inputs, and deciding how much to invest in different channels, do not assume that inbound and outbound-sourced pipeline will close at the same win rate, or in the same amount of time.


Especially for outbound as opposed to inbound, and especially for enterprise as opposed to selling to SMB, playing the long game matters. A lot. Sales cycles are long, rewards are lucrative, and you’ll never rush your way into a seven-figure contract. People who are used to measuring their work in quarters and years will be negatively affected if you approach them from a “weeks and months” mindset. Mirror the energy of who you’re talking to.

The context of how the buyer came to you is incredibly important.


Buying Committees Are Protective

Remember when you could send an email asking for the “appropriate person?”, and they’d just tell you?


And also, remember what happened as people started to get wise to this?


Understanding your Ideal Customer Profile (ICP) means more than just knowing who the business users of your product are, and at what specific types of companies. You need to understand not just the different people involved but also what their different motivations are throughout the process.


For example, Finance is almost definitely an evaluator (at minimum) in your enterprise sales process. But what do they care about when it comes to the type of solution you’re proposing they implement? And just because they’re part of the decision-making committee, should you actively prospect them upfront vs finding your champion first? (Probably not, unless you’re selling a financial solution specifically.)


Next, if your sales cycle is longer than 6 months, which it often is when dealing with the enterprise, then be prepared for people in your actual buying process to change. They’ll change roles, leave the company, and new stakeholders can be hired. Do “follow” people who left the company to their new organization even if they hadn’t finished buying from you. Don’t cold-prospect new hires to the buying committee, i.e. without contextualizing your message into the process that’s already underway, with the team you’re already talking to.


Brand Is More Important Than Ever

What does “brand” actually mean?


Even today, most salespeople scoff, quietly or loudly, at branding. That’s because they think of it as purely the visual identity of a company; the color scheme.


This is an incredibly short-sighted way to think about brand. Brand is reputation: of the seller themselves, the people they surround themselves with, their employer as a whole, and the product they sell.


You can cultivate reputation by keeping to your word, being courageous in taking risks that you believe you can accommodate and staking your claim to being one sort of person or another. Marketers, salespeople, and founders can all amplify their personal brands by writing online, speaking at conferences, or any other way of sharing their viewpoints and actions broadly.

Companies do this in the same way. They take actions, leave marks on their markets, do right or wrong by customers, and put their money where their values are.


Consequently, positive brand authority correlates to not just an easier time getting a buyer to take a meeting with you (because they are familiar with your and your company’s brand), but also a stronger win rate on opportunities.


For example, our own sales data at RevenueZen show that opportunities — excluding referrals — were either completely sourced or explicitly influenced by the founders’ personal LinkedIn profiles, were over 2X more likely to become customers than when not influenced by social media. This is a delightfully absurd advantage that sellers should pay attention to and leverage.


Negative brand authority works in the same way. If you or your company carry a reputation for dishonesty, poor support, or anything similar, then buyers will be offended at your very existence. Your product can still sell in spite of these factors, but it will be harder. You’ll be not only ethically compromised but also at a professional disadvantage.


Lead Generation in the 2020s


There is no one clear answer of what to do in light of these trends. My broad guidance is to remember to be quieter and listen, especially if you are earlier in your career. Look for the pearls of wisdom from people who have been selling successfully since the 1980s, while incorporating the innovations of those who are modernizing their approaches for the 2020s.


If you’re in sales, stay humble and remember that you can learn a lot from great brand marketers. Let them teach you how reputation, content, and message can influence others at scale.


Marketers, pay attention to what great salespeople are doing in one-to-one settings. They pay extremely close attention to the whole process, never hide behind a marketing automation platform, and remain incredibly human and analog throughout their dialogue with clients.


Sales development teams should take note: look at examples of fantastic SDR/content marketers like Sarah Brazier, currently at Gong. Forget the “smile and dial” bro floors of the past. Recognize that outcomes are difficult to measure in the short term and that quality of activity matters just as quantity does. Consider allowing your compensation plans to become more sophisticated in light of the balance between leading indicators like the number of dials made, and lagging indicators like number and value of proposals sent that were sourced by the SDR.


Finally, consider taking the adage “our secret sauce is our people” more seriously. Incorporate this wisdom not just into your current team and process but also into how you hire new team members. When hiring enterprise salespeople, don’t forget to treat the process and the candidates themselves like you would customers: have patience, understand their goals, and start with your perspectives and beliefs vs. your product. Teach them something new about what you know, while allowing them to do the same.


This is my call to you to take one step back, say hello to the product and marketing and sales teams you haven’t interacted with nearly enough, and bring your personal humanity back to what has too often become an over-systematized, over-quantified process.


Want to learn more about what makes a great enterprise sales rep tick? Click here to talk with Avenue Talent Partners about our thorough, people-centric approach to hiring the experienced enterprise salespeople the first time around.


Alex Boyd is the Founder & CEO at RevenueZen where he works with growing companies to help them scale their content marketing, sales development, and lead generation. Prior to RevenueZen, Alex was the Director of Sales at InDinero and has roots in finance and asset management. Alex was born and raised in San Francisco but currently hails from Portland, Oregon. RevenueZen works with startups all over the country, so feel free to get in touch if you’re interested in striking up a conversation with him!