Maximizing Sales Performance & Pipeline Management

I have been in the Enterprise Software sector for nearly 26 years, I have seen the good the bad and the ugly. I see a lot of challenges when it comes to hitting and exceeding your quota. There are so many factors that attribute to continued success and here are some observations I have noticed over the years, what makes the best of the best.

First off, there are so many factors that lean into an individuals success but in this article I want to unpack just a couple of focal points and I hope in future articles to unpack more.

Highlight areas I see needed to succeed in today's complex markets:

1. Deep Product knowledge - understand what your product does but more importantly what pain does your product solve for prospects.
2. Understanding your ICP - Knowing your Ideal Customer Profile is key to build your flywheel of success.
3. Understanding how to navigate and use resources internally - Knowing who on your team or in your organization that will help to support you from sourcing pipeline to closing the deal.
4. Master your sales process - Leaders spending countless hours trying to build the right structure for deal flow and the activities/steps it takes to carry a deal forward. Knowledge of the process is critical for successful outcomes.
5. Calling your Forecast - The best of the best do this with confidence and understand their path to the number. The complex element in this is compounded by the monthly and quarterly pressures one must face.
6. Pipeline Management - Day to day care and feeding of all the deals in play and the capturing of critical information to track and manage your progress.

Sure there are a lot more elements to making a great seller and the list could be 50 pages deep with topics like Negotiation, Enablement, Active Listening, Communication but I wanted to keep the list digestible.

The largest gap that I commonly see is that a seller is looking only 5 feet in front of them, the fastest moving deals with the closest close date. However, any fiscal year has 12 equal selling months/ 4 quarters to them and reps need to take a look at the world through a different lens.

At an executive and manager level there is constant conversations happening around pipeline coverage. Operations teams are crunching numbers and surfacing up KPI's around things velocity, win rates, conversion rates, coverage and many other KPI's. They will slice this data around deal type, product, selling cohort and many other levels.

The Disconnect:

What I have seen is VP's make broad brush statements like "You need 3X coverage to your pipeline" however that doesn't always align to KPI's or timing of revenue. As an example, I could go secure 1 deal that is 3X coverage for 2 years from now, and yes that will help you drive to revenue (potentially) in the future, but may not impact this years budget/quota requirements.

More often then not the actual details of the KPI's are not surfaced to the reps in the field and they don't understand how they personally can impact their own outcomes by these KPI's.

This leaves a disconnect between management analysis and the field actually understanding what all this means to them.

For the Sellers:

Beyond your current quarter/month, do some self analysis to understand if you have enough fuel in the tank (Pipeline) to sustain your number. Here is how I look at this:

Scenario 1:

Jane is a new seller who is fully ramped with zero dollars of pipeline and carry's a $1M quota. The average deal size for her segment is $50k with a known Stage 1 - Close conversion rate of 10%.

Do the math - how much pipeline do I need to hit my quota.

Now many sellers will tell me things like, I will just source bigger deals in my ICP and improve the close rate. I LOVE hearing this but history will show this is what her segment looks like. If Jane can improve the stats she will need less deals to obtain her number and we all HOPE she can do it. However, Hope is not a strategy!

When I did this fake scenario, I came back with a simple thought - Jane's quota isn't realistic unless she somehow can sell about 17 deals a month. I guess if she was selling very fast moving deals this would be possible but I am unclear on her path.

Scenario 2:

Jane is a seasoned rep at company Y, she has an existing pipeline that has different levels of maturity to it. with the same quota and average deal size her pipeline analysis may look something like this:

Conversion rates by stage should be materially different and can be a guideline for how much pipeline is needed to sustain her number for the year. It's a big difference on how much pipeline is needed in Stage 1 between the $10M in scenario 1 and the $1.27M in scenario 2.

Bridging the gap:

I could write an eBook on this topic but here are some ways to think about your path to pipeline.

Where to Stage 1 opportunities come from and do they have different conversion rates. The simple answer is yes, you will find in any data analysis that close rates will differ by source. Depending on your GTM model if you have both direct and indirect selling channels you will likely see a big difference for a variety of reasons.

As a seller know your path to pipeline:

• Self Sourced - this is commonly over looked because sellers are busy selling deals - right! Knowing your territory, ICP and using 3rd party tools like 6sense Demandbase , LinkedIn for Sales can help you quickly target prospects in market and heck, you likely have the networks to get your foot in the door.
• Sales Development - The SDR, BDR, ADR teams in your company is critical to driving pipeline they are the bridge between Sales & Marketing and the rubber really hits the road with this group. They are constantly running outbound and inbound motions to drive pipeline thus interfacing with marketing on key programs but also working with the reps to align on direction for their territory.
• Marketing - There needs to be alignment between the field and the marketing organization as they are running programs and campaigns daily to help source leads and interest in your products and services. If you are thinking of ABM as a strategy, there needs to be alignment between Sales and Marketing like never before.
• Partner - if you have an indirect channel of referral partners, resellers and even consultants they are a vital source of leads. I have found that these leads almost always convert at the highest rates because either they have held back on putting it in your pipeline until its way further down the line than a direct deal, or because they have an existing relationship with the end customer.

The company you work for should help you set standards for the best practices for obtaining additional pipeline, but at the end of the day they may not. Understand what you need to drive an outcome for yourself and share with your what works & what doesn't.

Advice:

Here is my advice to reps in the field:

1. Deeply understand your quota and compensation plan.
2. Know your territory through analysis beyond your internal data - ZoomInfo & LinkedIn are great places to start.
3. Understand your Ideal Customer Profile (ICP)
4. Use buyer intent to guide your prospecting efforts - G2 6sense Demandbase
5. Instrument your pipeline - either do it inside of your CRM through dashboards and reports or slip into a little excel to track your own KPI's for how much pipeline is required to hit and exceed your goals.
6. Collaborate with key groups who source pipeline so there is alignment.
7. Carve out 1 hour per day (minimum) to self source pipeline.
8. Be vocal with your leadership on the gaps you find.

This article wasn't designed to mitigate all of the other focal areas but rather take a look at how sellers need to breakdown their quota and the path to their own number.

If you have questions or want me to go deeper on this, hit me up on Linkedin Jason Rushforth