How to Sell in a Tough Macro Environment
aka Billy Robins Synthesizing Feedback from 4 Amazing Sales Leaders
One month ago, Software Snack Bites published a post called Borrowing From Other Budgets. It led to a very interesting discussion on LinkedIn led by Billy Robins, Head of Partnerships at Jellyfish, about selling in a tough macro and various tips that other sales leaders had. A sampling of the comments is in the screenshot below.
Needless to say, Software Snack Bites was not about to lose the opportunity to deliver Billy’s and his Sales Leaders friends’ insights to the readers of this here blog. So with that, we’ll turn this post over to Billy for tactical advice on how to best manage sales in a tough macro environment. Connect with Billy on Twitter and LinkedIn!
These are challenging times for high growth software companies to hit their numbers. Just this past week, Jeremy Donovan at Insight Partners estimates an SDR is sending out 1,000+ messages to generate a reaction. I talked to a number of sales leaders to get their input on how their teams are going forward and understanding who they are dancing with in a deal.
Universal truth; everyone has 24 hours in the day and a sales team has 90 odd days in a quarter. Well, let’s remove weekends and holidays. In Q4, the team has …. 61 days. This is exacerbated by prospects taking extended holidays and dealing with their own year end challenges. In short, teams have to work fast and more important, work smart.
In late September and early October, I consulted the following 4 sales leaders:
Kevin Nothnagel, VP Sales, Clockwise
Mark Kosoglow, CRO, Catalyst Software
Anon, VP Sales in SaaS & AI
Shep Maher, CRO at Betterworks
These were the 3 questions I posed:
What has been working the best in this macro environment to close customers?
How do you test whether you have a Coach, a Champion, or a Deadbeat in your deal?
In this “do more with less” environment, how does the team manage and still hit targets?
Here’s what I heard back and learned!
What has been working the best in this macro environment to close customers?
Headline:
Be creative, flexible and scrappy. Prioritize your team’s time.
Shep - “With the ability to send out so many messages, less experienced sales reps have a Sawz-all and they don’t realize it has power to destroy, as well as create. Buyers’ inboxes are literally flooded with generic “sequences” - AEs and SDRs send bland messages that lack personalization and can be spotted a mile away as an automated email. It’s BRUTAL! As a buyer, there’s no compelling reason to open an email, let alone respond and engage with a stranger. Do the work to personalize it. Make it hyper-relevant. Ensure there is a compelling reason to engage with you. And have a clear and simple ‘ask’.
Get multi-threaded as soon as possible. The larger the deal, the more critical this is. For my team, if we don’t have IT in a deal early, it WILL get shut down at a later stage.”
Mark - “I’m empowering my reps to win. I tell them, “The AE who makes the deal, wins the deal.” I don’t want them to do anything stupid because they are an owner, but they can get creative with buyouts, pushing start dates 30 days or doing lower year 1 pricing for an increase in years 2 or 3.”
Kevin - “Selling is coaching. You need to show people the path to buy, while also making it fun and engaging. First calls are a dime a dozen; you need to secure that next call promptly and with the right set of stakeholders.
Each deal is more precious; you need to treat SMB deals like Mid-Market opps and MM deals like Enterprise ones.”
Anon - “Be ruthless with your time and your team’s time. Strive to figure out what’s working, even if it’s a small improvement and then multiply it. Changes to first call deck generating faster 2nd meetings? Lean in and replicate it. Push for that 1% improvement each day.
Does your team understand what a good day looks like? Set those expectations - especially for less experienced AEs.”
Take-Away:
There's no magic solution. One thing consistent with all the sales leaders' was their tangible adrenaline and passion even through the Zoom. It's the maniacal focus on execution day by day, hour by hour that pushes their teams to raise their game and experiment with whatever works until it stops working.
How do you test whether you have a Coach, a Champion, or a Deadbeat in your deal?
Headline:
Provide tests to understand the unique deal dynamics and derisk your deal because it’s a fine line between Coach and Deadbeat…you need to figure this out early.
First let’s define Coach, Champion and Deadbeat.
Coach: Gives you feedback on your pitch and how you can do better in a deal.
Champion: Coach and then some. Helps you look around corners in an organization; makes your case when you are not in the room and views your success as their success.
Deadbeat: Appears to be a Coach (or a Champion), but when it comes to critical moments, they change their tune or even worse, ghost you.
Mark - “People use these terms (Coach & Champion) interchangeably; they are very wrong to do so. We need multiple roles and an exec in a deal; can they make that happen? If they can, Champion. You need to test your prospects.”
Anon - “Champions are effective agents that you can deploy to valuable effect. They can help you understand how similar purchases have been made. What matters to them + what matters to their leadership
You have to earn the right to make asks to your Champion / Coach. Do your research in advance and come in with a point of view of why you can solve problems for their team and company. Preparation combined with smart, timely questions earns you credibility with your prospects that you can convert into asks. Most reps don’t realize that Gives and Gets start on the first call.”
Kevin - “Do they give you access to information and power in a deal? When they commit to doing something to move a deal forward, does it happen?”
Shep - “If your buyer is using a competitor, and they tell you that they hate working with your competition, test it. Will they send you the competitor’s contract? If not, will they share pricing and the upcoming roll date? If they won’t do those things, you do not have a Champion and I question whether you have a Coach.”
Take-Away:
In this “do more with less” environment, how does the team manage and still hit targets?
Headline:
Minimize surprises by seeking out friction; even if it’s uncomfortable. Act like an owner; find a path forward rather than focusing on the challenges you are facing.
Mark - “Close easy deals. If you have a path to a favorable deal in week 5, take it. Get the CARR on the books, make progress towards your quota and have more time to work the complex deals and/or chase the swing deals that are a critical part of any great sales quarter.
It’s hard work; people don’t want to hear this but the reality is that it’s going to take some grinding to deliver right now. Get to friction fast.
Role play the business case + pitch with your Champion; the first time they deliver the pitch should NOT be to the Executive Buyer … help them sharpen their saw.”
Kevin - “Run a MAP – either homegrown or use a purpose built tool like Accord. Focus on speed; how quickly are you responding to in-bound leads?”
Shep - “In this environment, buyers may not be able to buy on your timeline. Make sure your team does the work but realize great reps may only be at 80% in this market. Like a baseball player who is in a slump, your team needs to maintain confidence and composure in your value prop and the sales methodology. Stick to your routines; don’t panic. The seeds you are planting today may not bear fruit tomorrow - but they will bear fruit at some point in the future. Keep on grinding and good things will happen.”
Anon - “If you don’t understand how momentum is maintained in the org … time kills all deals. Understand the realities of change management, if you can get the conversation past the easiest stage (close the deal); what do you do for rollout, what’s the project management and risk look like?
Ask questions like: What’s your point of view on how we start to socialize this from stakeholders to get this approved?
Ask strong users to meet with your best prospects. Keep it simple. 1) Express gratitude for their business and 2) Ask for referrals in a live conversation.”
Billy’s Note - In a tough selling environment, teams should almost exhaust the referral motion before they get too exotic.
Take-Away:
The compressed Q4 timeline means in order to succeed you need to find & close the “easy” deals as soon as possible, find out who is on the other side of the table and seek out the tension in a potential deal cycles, all while practicing good sales fundamentals.
I hope this was helpful to all readers. Please feel free to reach out to me (Billy Robins) on Twitter and LinkedIn if you’d like to discuss further. Also, I welcome all comments and feedback as we are all trying to improve and continue to push forward!
Hi Shomik! Thanks for sharing this. Very insightful.