Highlights:

1. Have a regular sales cadence of what should happen throughout the year so your team can plan, other divisions such as product and marketing can align to your sales requirements and you have a strong grasp on your business
2. Pipeline reviews aren’t just for looking at what’s in the pipeline already; they’re for constantly planning on what will be done to increase the pipeline
3. A great sales leader has to wear many hats; strong deal coaching skills and accurate forecasting are two you need to be comfortable wearing 

Jennifer Bers is a Notion GTM Expert with more than 20 years experience leading sales teams for innovative, fast-scaling SaaS organisations. She supports Notion portfolio companies to create and grow high performing sales teams, with an emphasis on empowering leaders and reps with coaching, feedback, training and leading by example.

Truly scaling a business means predictability

Most people think of predictability in terms of revenue, of forecasting and of deals closing.  Of course those are important. However, getting to a point where you can genuinely say that your business is on solid ground and scaling also means predictability in operating cadence so everyone knows what is expected, when and how - every year, quarter, month and week. 

I’ve been asked many times by sales leaders “what should I be doing?” That’s not as obvious an answer as you might think. Of course meeting customers, prospects and spending time with the team is paramount. But how do you ensure that you’re creating a well-oiled machine, rather than racing from deal to deal and crossing your fingers that things will work?

QBRs at the start of the quarter are a must, which we covered in depth in a previous article - How to run a QBR people genuinely want to attend. But what should you be thinking about beyond that?

Annually‍

Let’s start at the top, what should you be doing every year?  

Three absolutely must dos:

1. Evaluating your TAM

This is to ensure that you are honing in on your addressable market, highest priority segments and of course your ICP, aligning your whole organisation (Marketing, SDRs, Sales) on who you should be going after and why; has your expanded product capabilities created new ICP; have you honed in on customers most likely to not only renew but expand, etc. Review the accounts that came in during the previous year and see if there were obvious outliers who maybe aren’t a good fit and you know you’re spending too many resources and time and trying to make your solution work when it probably really shouldn’t be where you’re using time.  See who did come in, where the leads were sourced and what messaging worked. Refine, refine refine.‍

"In today’s data/metric driven world, sales cadence is probably more important than ever. When done well it provides the mechanisms to understand not only the quantitative information you need but also the qualitative information as well: the ‘feel’ of how things are going. What’s the market perception of a new proposition? What could be improved? How is everyone feeling about the year and how to achieve their numbers? Who are the competitors and how are they evolving?  Todays’ world of technology is morphing faster than ever so measuring data is only useful when seen in conjunction with the real-world experiences".  -Roger Walton, CRO, Resistant AI

2. Territory & Quota Assignment & Comp Plan

Each year, Sales Leadership should review the TAM and ensure that the correct accounts are being targeted and focused upon. Territories can be refreshed adding in new accounts or reassigning those that haven’t had the right level of engagement.  (Note, this can also be done more frequently). You’ll also want to provide the team with their targets to achieve annually, quarterly or monthly depending upon the sales motion of your company.  Larger more complex enterprise sales likely will have an annual target to allow for the longer deal cycle. If your deals are smaller and more transactional your targets may be quarterly or monthly.  You’ll also want to ensure the compensation plans align to this.  Remember, compensation plans drive behaviour so please think through all the ramifications of your plan and how they align to your desired outcomes.  Yes, your reps will work to understand how to maximise their earnings and success from the comp plan. No, this isn’t unique to your company. Just know every rep will tear your comp plan apart and as long as you’ve planned for this and are driving the right actions with the right reward as a result, you’ve designed a good compensation plan. This might be a good topic for a future post.

3. Resources and bottom up planning 

I’ve seen many founders just take the number they want to achieve, divide by the number of reps and that’s the quota.  Unfortunately, that’s not really how it works and you need to make sure you have the right number of reps hired or in the pipeline to be hired. Great sales leaders are always recruiting and have a bench for when they need more talent. A lot of this  planning is math—ensuring you have the right capacity, or in fact overcapacity. It’s naive to think that 100% of reps will hit 100% of their number 100% of the time. That’s just setting sales leadership up for failure. Things you’ll need to consider: new rep ramp times;  the average deal cycle and average deal size; how many reps you have; how many deals realistically can they manage at a time; anticipating AE churn; at what point in the year do you hire these reps, what is the planned inbound/outbound lead funnel; what’s the conversion of those leads, what percentage of these leads convert and close, etc. You’ll want to over-assign quota (quota capacity, or “street quota”) knowing that a percentage of reps will be ramping or won’t hit.  Yet another topic for a future post.

You should also think about defining Success Metrics of what you’d like to achieve.  This might be a certain number of new customers per rep per quarter or what percentage of accounts should be Enterprise level v Midmarket (if applicable).

"An effective sales cadence is critical for building the right success habits across the sales team, which compound over time into a high-performance culture; achieving goal just becomes something that happens routinely as everyone's individual routine ensures it does.  It's also critical for identifying risk and course correcting where needed, in addition to getting all stakeholders pulling in the same (and right) direction by aligning expectations and execution across marketing, customer success, finance, and sales teams". - Sean Bennet, SVP Sales, Triptease.

Quarterly

QBRs are a great way to start the quarter–it gives everyone a chance to reflect on the previous quarter and create focus on the upcoming ones.  I wrote a separate post on this so won’t go into depth here.

Depending on the maturity level of your company, and types of companies that you’re selling to, reviewing Account Plans and Territory Plans are best done on a quarterly basis. Note: Great Account Plans are NOT cutting and pasting financial information in from Wikipedia, nor is it a static document that lives as a link in your CRM to be dusted off only when the review happens.  If done well, they’re a chance to delve into the growth and motivations of the account, where they sit competitively with their peers and brings the whole organisation together to plan for growth.  This will be a future topic as a paragraph isn’t going to do it justice.   

What does a great Quarter cadence look like?  In all honesty this will depend on the type of business you’re selling. Very large Enterprise deals aren’t going to make sense having quarterly quotas. Likewise, smaller transactional deals probably make sense to have monthly targets.  Traditionally there are quarterly targets, and you want to avoid the typical hockey stick with all deals closing at the end of the quarter.  

"For companies that have quarterly targets, avoiding the typical hockey stick where deals close at the end of the quarter, is key to building a winning cadence.  A healthier approach that I've aspired to is to have a closing focus in month one, hit quota by month two and use month three to prep and build pipeline for the subsequent quarter. Ways to do this include: over-incentivising month 1 closes, ensuring Action Plans are in place day 1 of quarter for rollover deals and driving initiatives and gamification to create urgency." - Adam Kay, SVP Sales, Paddle

Monthly

Pipeline Development Planning.  Which are the key accounts that you’ll be targeting and how do you plan to reach them?  Sales should also be constantly ensuring that they have enough pipeline to avoid the ‘desperation pitch’ at the end of the quarter.  Once you have enough data, you’ll be able to tell your close ratio. I don’t consider deals in ‘Discovery’ to be considered a qualified opportunity–that’s the point of Discovery. Once it moves to the next stage I know that the sales rep has qualified it and there’s a real deal to be done.  As a rule of thumb, you want at least 3x your quarter’s quota in qualified opportunities. If you’re really on top of things, you’ll have that for the following quarter as well.

Weekly

This is where great leaders separate from the good. There’s a LOT to do each week.

Planner:

I start the week with a simple planner that’s open for all to see. Nothing fancy–just a Google Sheet with each rep listing: what new logos they’re meeting this week; what follow up meetings are happening; how much pipeline was created the previous week; one thing they want to accomplish this week and did they accomplish last week’s goal.

Yes, this can probably be pulled from Salesforce. But I prefer it as a sheet everyone sees because it lets everyone know who we’re meeting and opens the discussion up, and also psychologically there’s something that happens when you’re typing in all the new logos you’re meeting. Or not typing anything in.  3 weeks of not meeting anyone new is a huge leading indicator that something is wrong.

1:1s

I try to get at least 30 minutes with each of my direct reports. This is THEIR time.  What do they need from me, what roadblocks can I clear. How are they doing?  When I can I much prefer to have walking 1:1s–we all stare at each other across pixels way too much. Getting a nice walk in while talking, even just as a phone call, somehow can unblock conversations that might be stilted sitting across from each other.  Also, put your ego aside and ask for what you can be doing better as well!

Pipeline Review

Sales Managers should have a pipeline review each week. Using whichever qualifying methodology you prefer: MEDDPICC, SPORTSMAN, CHAMPP, ensure that the deals really are a) real b) in the right stage and c) in the right date for closing.  And every other week—instead of looking backwards at what’s in the pipeline, focus on what will be coming in.  Which accounts are they targeting? How did previous pipeline generation efforts go? What worked, what didn’t and how will they target this new group? Who else needs to be involved to help get these prospects talking to us?  

Pipeline review is NOT just a look at what you have, it’s looking at what you SHOULD have or are aiming to have in the pipeline soon.

Opportunity Coaching Sessions

This is the meat of what great managers do. Help the team think through their deals, spot gaps and figure out how to move deals forward in a professional and advantageous way. One helpful way to do this is to have a checklist for reps to fill out before the session and send to you to review so you can do your own research on the company.  Remember, this is NOT to make them feel caught-out—otherwise what will happen is they’ll hold back on telling you the bad news. Nor is this telling them what to do next. (well, hopefully not). True coaching is asking the right questions so the rep delves deeper into their understanding of the deal, the gaps and then tells you what needs to happen next.

Forecasting

For first line managers, this might coincide with the pipeline review.  For second line managers it’s pulling together your management team and being able to reconcile a forecast across multiple teams. Great managers will know which reps have a tendency to sandbag or those with happy ears. Yes, your CRM should be accurate but we all know that there are often discrepancies. Besides being a great coach, one of the most important aspects of a great sales manager is the ability to truly forecast their team’s results and understand what will come in this quarter, what will slip and what they’re working on helping the reps qualify out because it will never close.

In conclusion

It’s pretty rare that when I ask reps about their career goals they don’t say ‘management’. When I ask why, it’s usually because they want to be involved in setting strategy.  

As you can see here, sales management at the Director/VP level is rarely about strategy. It’s about ensuring the trains run on time, the trains run smoothly and predictably and the whole organisation knows what to expect from each train’s cargo.  

Without a strong operating cadence, that’s almost impossible. These are the fundamentals that make a strong, predictable sales organisation hum, and makes standing in front of the board each quarter an enjoyable experience instead of a really tough conversation.

You’ll find working with great sales leaders and trainers that you’re constantly picking up best practices and I’ve learned from some of the best–thank you to John Kaplan, Jay Tyler and Kevin Wood