Winning in Enterprise Sales

1 May

Sales Talent

Sales Led business culture.

At CloudSense, we became good at selling. As the company grew, we had a remarkably low customer acquisition cost and remarkably high customer lifetime value. In other words, we had an efficient sales team that massively outperformed the market norms in terms of quota retirement, and an outstanding record of getting our happy customers to continue committing to more and deepening their relationships. A good sales team and sales culture was something respected by the whole business, and we prided ourselves on being both “Sales Led”.

Here’s what I mean.

Being “Sales Led.” meant that our sales team became a bellwether for the ongoing needs of the customer, which inevitably changed over time. I felt it was important that the entire business should seriously listen to the sales perspective on what we were doing because it avoided the traps of product ideologues and engineering “ivory towers”. This inverted the model I’d experienced in other businesses, where it was common to diminish the view of sellers who ‘just couldn’t sell the product’. With caveats to these last statements being we needed the right controls on quality, market research and qualified customer need; sales can be the best source of the innovative ideas that drives product thinking, business growth and retains customers.

Here is my own quote from our sales onboarding literature:

“We have a sales-led business culture. It means we focus with energy on the customer and what they want. Every department is asked quarterly what they are doing to enable the sales teams to sell, and they are held to account for what they do.”

Part of being Sales led meant every department needed to be easy to do business with, in the eyes of the customer. In the way we engaged, contracted, and delivered solutions, we would be accommodating to the needs of each customer, provided we could keep our product and service integrity, and it was commercially beneficial. It was like walking a tight rope some of the time, but we never dismissed a customer’s request, we were open and innovative about our solutions matching the value they needed, even if we needed to adapt to do so.

The Challenge of Hiring Enterprise Salespeople

When my company started, I was one of four co-founders. We all wore many hats, but I was the “front man”, it was my job to sell. Though not a trainer seller, I am a good listener, a creative person, and a quick enough thinker. A combination of these attributes meant doors started to open.

We’d passed $1 million in sales when I realized that I could no longer do it all myself. Our success had created a growing organization with mouths to feed, and we needed to keep up our rate of sales. From that point on finding good sellers was mission critical ad there was a lot of trial and error to find great people, train them, and make them successful. It took several years to understand the most attributes of a good seller. Sellers are often best at selling themselves at interview, so learning to cut through this and understand if they could sell the product took patience and learning, this is the sales shopping list I came up with.

· In a word, Intensity.

· They were competitive. They wanted to win in deals against the competition and against other salespeople, where they wanted to stay ahead and show that off. We hired people who thrived on going to get a deal done for the love of winning.

· These people had a high work ethic, with good foresight and planning around what was needed in the deal. They thought of, committed to, and executed on all the tasks to get a deal done much better than other people.

· The best salespeople were curious. They wanted to learn more about our strategy, our solutions, the customers, and their businesses. This came from their desire to win.

· We tried to hire salespeople who were unafraid to aim high, in terms of the customer and deal size they’d go for. They bought into the idea that it’s just as time consuming to sell to smaller mid-market targets as to big brands, only big companies have greater expansion opportunities.

· During hiring I began looking for people who were nonconformist. Good salespeople were unlikely to be role models for administrative skill and process adherence. They’d look at situations and opportunities in unusual, interesting ways. This self-centred approach to their own deals was a productivity multiplier.

· Good salespeople were passionate, which often meant they were opinionated and could be a handful. Though that’s a liability, it’s one I concluded was worth managing, because the upside was someone who could build emotional connections with buyers.

Enterprise Account Management

When our best salespeople ran a customer account well, it looked something like this.

· They’d be team players who coordinated with their colleagues in business development (BDRs) around an account they planned to expand, getting help to build intel, points of contact and relationships.

· They’d keep walking the halls within the account as an opportunity progressed, earning the right to navigate relationships up through the business and across leadership. This was the only way to mitigate the big risk of partial knowledge causing failure.

· They’d always be expanding activity and contacts in their opportunities. Those who spent more time searching for information, building more relationships, and appreciating the power dynamics and individual wants and needs, created the alignment and cohesion in selection processes.

· Our deals were often won and lost long before the final executive “pitch.” Good salespeople knew the executive pitch should be a hygiene factor to seal a deal rather than a game changer to win the deal itself.

· Keeping up momentum after selection took discipline and meant agreeing a “diary of events” with the buyer, milestones leading to signed paperwork. Those at the top of our leader board would know it, revisit it, hold people to dates, and keep working on solutions to inevitable procurement and legal issues until the paperwork was done.

· Sales consistently exceeded quota when they kept on selling to their customer base, having a plan to expand, and working with business development. The best way to keep an account from churning and the easiest way to hit quota was to focus on where we were going together next. It was cheaper to keep and grow an existing customer than land a new one.

Leadership and Selling

As the CEO, there were times when I had direct responsibility for sales and as we matured times when others were running sales for me.

It’s easy when your company grows and gets more complex, to become very involved in the daily operations to the detriment of selling and growing. You can find yourself dealing with the consequences of intensive growth on internal operations, only to see new growth dissipate

I was drawn time and again back into business development, and with hindsight believe our success was in large part due to this. When it comes to growing the business, I believe that founders must lead by example.

There was always a correlation between the growth of our business and the time I spent on selling. I saw this frequently over the years: when I would drive growth and then be sucked into the operational impact of that growth, and new sales would tail off. No one can super-size a start-up better than those who conceived it.

As founders, we were the secret weapon of sales. We were at th4 centre of our culture, and everything the business stood for. Our roles meant we got listened to, ahead of everyone else in the business.

The most useful times to be involved in opportunities I think were right at the start, setting up the benefits case for the customer, the value sell. I’d do this as a helpful initial exploration with the buyer around what they wanted to achieve, helping paint a picture of a future state for them, differentiated by the critical capabilities we’d bring, and the results they wanted to achieve. Having driven an engaging dialogue that could inform a business case and the buyer’s ROI, my team would be left to get on with it.

There was always a lot of hard work to do in any deal after that, and our salespeople would be driving hard at every stage. But when the time came for the buyer’s decision maker to commit, I needed to be involved again.

Working towards an executive sign off meeting created a compelling event for the rest of the team. It was a show of commitment from our company to have a founder sponsor this work with the buyer and one that created a lot of buy-in and commitment to us in return

It would be my job to lead that discussion, to revisit the learnings from our first engagement, to promote all the hard work and progress that had happened since, and then to ask the customer for their business. This doesn’t come naturally to everyone, including me, but it was an essential part of moving forward into getting contracts done.

Enterprise Sales Motion

Code Breaking

Learning the difficult behavioural code of finding and motivating good salespeople was the first challenge, but as the team grew, I really needed to work out how to keep them focused, motivated, and accountable for growing the business. I learned that doing this took more than just a CRM system for pipeline management; it required a lot of elements coming together.

“Sales motion” is a term I once heard used to describe a holistic process for all these elements working successfully to make a sales-driven business, and I found it very helpful as it created the picture of a set of moving parts working in a system to make sales happen.

It took me a while to understand this holistic process. As a new business, I didn’t have to forecast to anyone how likely we were to land a deal, and if I were asked, the reason behind the question was less about hitting a target and more about whether we’d be in business in three months. When I hired our first salesperson, it was my responsibility to understand from them whether their work would generate sufficient sales to keep the lights on. This felt like a big responsibility, but I didn’t know what to ask to them.

Early conversations went like this:

“Will that deal close this month, like you said?” I asked.

The answer was invariably, “Yes, I think so. The prospect definitely likes what I’ve proposed.” (Always said with a big smile. After all, I was talking to a salesperson.)

But with no frame of reference, I was never any closer to knowing if the deal would get done that month or not. My only choices were to shadow every sales meeting and judge where things were, or else back off and keep my fingers crossed that everything would be okay at month end. Neither were great options for a little business clambering from one cash squeeze to the next!

We bought a CRM system, and I asked our sales guy to write everything he did down in that system so I could predict the rate of success in our sales. This gave me a comfort blanket; with all the hard work going into prospecting documented in one place, I didn’t have to ask for an opinion about month end. With the data at hand, I could form my own opinion. Salespeople often look for the path of least resistance to getting paid, and in this case, as the eager boss holding the purse strings, I said (in so many words), “As a condition of getting paid, you fill in CRM.” So, of course, it got done.

The result was I’d taken sales time away from prospects and put it into record keeping, so that I felt in control; but it made no difference to the outcomes. Some deals closed, some didn’t, and if they were kept up to date at all, the expected close dates in our CRM seldom reflected when contracts were signed.

After I pointed this out with little humour to my growing sales team, I started to see another pattern in our data. New deals would appear from nowhere in the system with a close date no more than a month away, and then lo and behold, they happened! And on time! It turned out that salespeople would keep a deal “off the books” until they were sure it was happening, and then enter it in the must-use system at that time. Whilst behaviours had shifted to keep the boss happy, I was no closer to knowing accurately when deals would close any more than a few days ahead of time.

Salespeople were at least trying to keep their paymasters happy and begrudgingly using the system, even though it took them away from making sales. But worse than this, I believed that quite a few people in the company, me included, had valuable contributions to make to moving our sales forward, but it was never clear how and when this should be done. The team was malleable enough to follow what I was asking, so I knew I must be asking for the wrong thing, because we still didn’t understand how to make salespeople accountable for what they’d sell and when.

By our third year, we had a sales team of five, and we’d hired into our management team as well. To broaden perspectives, I encouraged my management team to make contributions not only in their respective fields but cross departmentally. Consequently, I listened intently to one of my management team explaining to me that we needed to control the sales process more by making salespeople tick the things we wanted them to do in each deal from a list that tracked the initial opportunity through to closure; “Elevator pitch,” “internal approval of product and pricing,” “discount offered,” and more.

I agreed. It wasn’t long before I regretted having used tick list micromanagement to try and detail all the internal steps, we wanted sales to use to prove they were selling. I was beginning to realise that in a sales-led business, many people who have never held a quota are more than happy to offer an “expert” opinion on how to run sales. The sales team who’d been compliant in the past objected. I was asking them to administer a list of internal tasks that weren’t central to the work of selling. They were right—the process didn’t help us understand or act. Instead, it sucked time away and demotivated our salespeople, who felt mistrusted.

Cracking the Code

Following my earlier attempts at building a sales process around a set of administrative checks, I’d been on the lookout for a better way to organize the work of the sales team, something that could create a useful set of interactions from which salespeople and managers could benefit.

By this stage my board consisted of founders, four investors board directors, and an independent non-executive. I knew the external directors each spent a lot of their time with growing start-ups. After one board meeting, I approached each of them separately saying I wanted to learn more about what a good sales process might look like - that we needed something better than a list of procedures to follow as a deal progressed.

My ask from each of them was to help me get educated by businesses that were doing sales well.

After a few days, my independent non-executive director identified one of the companies he’d done sales coaching with, and my VC director identified a portfolio business that had been through an upgrade of their sales process. We fixed up calls with each company, and these conversations proved to be very enlightening. What I learned became the basis of a new healthy common narrative between management and sales.

I learned that without a good way to organize the progress and activity of each sale, I’d continue to be unable to engage the sales team in a repeatable dialogue. Without a repeatable dialogue it would be hard to spot recurring deal blockers, discuss and coach on deal tactics, champion the successful behaviours that had resulted in wins in other similar situations, and learn from competitor tactics when they’d beaten us in the past.

A good sales process is an enabler for structured positive coaching conversations between managers and sales that create mutual understanding and deal progress, and as a by-product deliver accurate forecasting of probability and closing timelines. This is the opposite of asking a salesperson to state out of context when a deal will close. It’s a facilitated conclusion.

Creating the structured process and positive coaching conversation requires both the common language and the map of the customer’s buying journey, divided into understandable stages, with details of what is needed from your team at each stage and identified customer expectations for that stage.

The MEDDICC System in Enterprise Selling

MEDDICC is an acronym that stands for metrics, economic buyer, decision process, decision criteria, identify pain, champion, and competition. Developed by Jack Napoli (the “Godfather of the MEDDICC sales process”) and his business partner Dick Dunkel, MEDDICC became an effective framework that we used to anchor our sales motion as deals unfolded and we worked out what to do next. It guided our prospect/customer through the buying process, opened our eyes to what we didn’t know about our opportunities, and helped us close faster and with fewer unpleasant surprises.

Here they are in detail. Please note the action items are not in strict chronological order. We described it as more like planting a garden in stages, where you need to simultaneously nurture groups of little sprouts into healthy plants:

Metrics

This describes improvements in revenue, cost, risk, and/or productivity that the client will experience. It’s the quantifiable business results of the solution (ROI), and how the customer will ultimately measure the success of the solution. The customer should have a sense of urgency about attaining these results, and avoiding the cost of doing nothing.

Example:

Increase avg. deal size by X per cent.

Reduce X per cent of abandoned orders.

Improve NPS by X per cent.

Reduce order error rate by X per cent.

Reduce operating cost by X per cent.

Consider: Have the prospect (ideally the economic buyer) and we agreed on the measures of success, and are they compelling?

Economic Buyer

This is the person or group qualified and required to give the final “yes.” The ultimate decision-maker(s). They own the budget, have authority for discretionary spending, and can re-allocate funds. They care about the bottom line for the business, and want to know how much, how soon, and how sure the business benefits will be.

Before adopting MEDDICC, countless hours were wasted when salespeople ran lengthy engagements with people inside target businesses, only to have the person sign off by saying, “That sounds great. I’ll take it to my boss/supervisor/manager and get back to you.”

Consider: Who is funding this initiative, and are they aligned to the needs analysis and metrics (value case)? Do you have access to them?

Decision Process

This is the prospect’s process for researching, evaluating, selecting, and purchasing a solution. It includes the steps, the timeline, and the people who will be involved in the decision-making and the purchase/PO process. It establishes the roadmap for selling activities (calls, meetings, demonstrations, value-based needs analysis workshop, contracting). Critical for forecasting accurately and avoiding last-minute surprises, it should be discovered early and validated often—it’s never “one and done.”

Failure to understand the decision process is the number one cause of slipped deals and unpleasant surprises near the finish line. We’d map it out—using realistic timelines—with our champion as part of our mutually agreed-upon close plan, known as “the diary of events.” Beware of vacations, backlog, and competing priorities.

Consider: What are the specific steps the prospect will take to make a decision? Who is involved and what is their timeline? What is driving this decision? Have you and the champion documented the purchasing process and timeline? How long did the last purchase of this kind take within the client?

Decision Criteria

This is the list of prospect requirements that all competing solutions will be evaluated against. Defined by the prospect but whenever we could engage early, influenced by us based on our understanding of the prospect’s needs and our solution, including how we solved their challenges better than the competition, using our differentiators. It should include financial, technical, process, and vendor-related criteria (quantitative and qualitative), and ideally be ranked/prioritized and focused on the minimum requirements.

Consider: What are the customer’s needs are they well aligned to your proposal from a capability, financial, and organisational alignment perspective? How are you influencing those needs?

Identified Pain

These are the critical business issues that are the catalyst for a buying decision. We spent time identifying and quantifying the largest points of pain, because large pain/challenges => urgency => budget/action.

The pain point should be measurable in terms of the things the economic buyer cares about: revenue, cost, risk, productivity. Use open-ended, two-way discovery questions to uncover pain. Though this is the first element of MEDDICC to investigate, keep asking, “What would you make better if you could? What are the points of friction?” and similar questions throughout the deal

Champion

This person is an advocate, with influence, who’s in favour of the solution. (The descriptor “with influence” is critically important. Someone who has no influence cannot be a champion.) They have their own personal goals and motivations, value drivers for the solution. They provided access to information and people, and—even better—would sell on our behalf inside the company where we had no access.

They need to be identified, nurtured, and regularly tested by you.

Consider: Who is your champion? How do you know they are a champion? What are you doing to nurture and test them? Is the economic buyer their ally or opponent?

Competition

This is who you’re up against—their strengths, weaknesses, and differentiators. We used our competitive intelligence resources to understand them technically and commercially and used our champion to understand them politically. We’d discover their champions within the target company and make a plan to address them, such as asking trap-setting questions that highlighted our unique value and differentiators (how we did it better).

Consider: Who are your competitors and what is your strategy to eliminate them? How are you preventing “no action?”

These seven action areas within MEDDICC represent a well understood set of discussion topics that can become the basis of deal research, planning, tactics, and coaching. Coaching on the best way to handle each given topic and improve understanding and control of the variables is an important step away from vague, open-ended questions and answers, and a big move towards a thoughtful and forensic assessment of every opportunity you’ll work on.

Eight Enterprise Sales Stages

On its own, MEDDICC gave us isolated insights, but it didn’t give any sense of what needed to be done nor a journey to take through to a sale. What we needed was a format to guide and control the sales process to success. The second aspect of the sales motion—mapping the customer buying journey into understandable stages— is something we built out with the input of our best salespeople and their experiences on the ground. The following represents the sort of thing we did. It majored on the act of selling (not the admin) and activities that went into that, and it created neat “gates,” which were the staging points to look back and check what had been achieved so far and to look forward at the next things to do.

1. Find an Opportunity

At this initial stage, the owner of the opportunity was the person whose job it was to go find early- stage prospects within an account territory list. This may have been anyone in an outbound go to market team (in our case at scale, a BDR or alliances person, a customer success manager, or a sales person.) At the top of the funnel, we expected such early-stage opportunity to be coming from a mix of people.

Their objective was first to find an identified pain, and then the key MEDDICC elements around it: the metrics, champion, and any competition. The owner was responsible for checking the prospect met our qualification criteria of size, industry, need and so on, to avoid wasted effort from the start. When this work was done, if a seller was not the originator there would be a hand over meeting where they’d accept the opportunity or give feedback as to why they were rejecting it.

2. Find a champion

By this point the owner of the opportunity was the salesperson. Their objective during the second stage was to find the right person to champion the value added by our business and have them agree to bring in their wider business team and work with us on a business case for fixing the identified pain.

By reconfirming priorities, objectives, and existing systems from the first stage the seller could envision a future with the champion, where we’d address their identified pain in a valuable and different way and earn the right to expand the conversation to wider audience.

This happened through dialogue and at that time, the seller would be learning more through that process to enrich the key elements of their CRM opportunity—the identified pain, metrics, champion, and competition and the prospect’s decision process.

Once the business champion agreed and diarised a deeper “needs analysis” workshop alongside colleagues, then the exit criteria had been met to leave stage two.

3. Agree Value

The objective of stage three was that our team and the prospect’s stakeholders needed to agree the value our product could add, with a business case confirming that we were well placed to deliver success for them.

Our salesperson needed to do the work of preparing for the business case workshop, by learning more about the people involved, their KPIs, the change they sought, and the value calculation that elaborated future results potential.

The needs analysis workshop followed a process, beginning with the value drivers—what the customer wanted to achieve, then a review of the current situation and identified pain preventing their achievement, and their barriers to growth, profit, efficiencies, etc. Our team would explore a vision of the future, with our products and services mapped to the desired outcome for their company and stakeholders, in a way that was different, and competition couldn’t match. The output was a set of mutually agreed numbers expressed as a business case.

Ensuring a realistic business case and successful future state required considerable coordinated work effort, and the workshop was often divided so detailed playback of the desired future state happened later.

To exit stage three, the business champion would need to confirm support for the findings and recommendations of the needs analysis and as a result schedule a presentation and/or demo with wider key stakeholders.

4. Build Support

The objective of stage four was to extend our influence across the field of prospective decisionmakers and influencers and connect our executive team with them. Selling technology, we needed to convince business and IT’s senior team and decision makers that we could overcome their pain, and deliver value. We’d rely upon a reasoned business case, our customer testimonials, and pinpointed software demonstrations showing our value to do this. This work needed to neutralise the competition, building support for our solution.

Opportunities reaching stage four, consumed a lot of our business time, connecting with senior people, validating and demonstrating the future state we’d bring. So updating the key elements of the opportunity, including the decision process, economic buyer, and decision criteria remained essential too to ensure requalification. Stage four opportunities would be forecasted with a heightening probability of being won and attract increasing internal scrutiny.

The exit criteria for stage four was that the business and technical stakeholders confirmed their commitment to the business case, desired future results and that the solution met their decision criteria/minimum requirements. Importantly, we’d need confirmation that our solution had been selected.

5. Confirm Intent

Reaching stage five, the salesperson would need to get confirmation from the economic buyer, that they believed in the business case and would proceed with a purchase. This meant asking for the business - usually this happened, either in a final presentation or at an executive one- to- one meeting.

To complete and exit the stage, the economic buyer confirmed they would now buy from us, and we’d also agree the customer’s purchasing process to enable a smooth closing phase.

6. Close Deal

The objective of stage six is that prospect’s buy team agrees to a time-bound close plan. The paperwork gets created and agreed, and final pricing is also agreed, both internally and with prospect. Using the opportunity information, the salesperson would keep the internal team up to date on the purchase process as well as any other changes. Deals can slip or fail even at a late stage, and the salesperson needs to work with energy and intent to deliver the agreed diary of closing events, coordinate with legal staff on contracts, reconfirm process, present best and final pricing, and draft order forms.

To exit this stage, all concerns must be resolved to the extent that the buyer’s team accepts and signs the paperwork.

7. Customer Welcome and Handover

Stage seven is key to future growth because its success determines customer success and renewal probability. The objective is that all paperwork is confirmed as having been signed accurately and stored in CRM for future consultation. Payment process details are confirmed and actioned, and hand-offs to internal teams for activation, project start, and customer success are done. Once assigned, the post deal engagement team would be responsible for a strong customer welcome and initiation.

To exit this stage, executed commercial paperwork is verified and stored in CRM, and hand-off to downstream teams have been started and the customer gets positive onboarding experience. This stage needed to be completed for sales to get paid commission.

8. Abandoned Sale Review

Not every deal gets won. At every stage in the pipeline there will be drop out as the exit criteria cannot be met. Such deals needed to be understood, and the further through the stages they’d advanced, receiving resources and heightened expectation of winning, the deeper the review.

The owner of abandoned sales reviews is the sales leader and the review process also includes product management and the salesperson.

Improvement Opportunities

In the early years, this final ‘abandoned sales’ stage was often overlooked or taken lightly. But having had poor conversion of stage one opportunities handed over by business development, our leadership team kept returning to this subject in management meetings, and we agreed that we could reduce our customer acquisition cost by adapting behaviour and being focused on continuous pipeline improvement.

It was hard and took honesty to do a disciplined analysis. Making the change was met with tension in the sales team. It began to work as we moved to having a coached environment with good guardrails around our process, so that a loss became visible through ongoing deal dialogue. It wasn’t swept under the carpet after a sudden unexpected loss. It was a tricky balance for competitive people who don’t like to talk about failure. The key was to help the salespeople embrace the fact that they would earn more if they learned from losses and become better.

The reviews centred on why the sales investment didn’t result in an order, creating incentive to product and sales leaders to improve marketing and innovation and become a more competitive organization. These important reviews went into some detail and relied on the salesperson providing more information on the opportunity, and because sales could not select this stage without completing that information, they had to provide it or else continue to be held accountable for it as a live deal.

No one deal could be relied on for insight to improve the chance of winning in future. We needed trends, played out across our many deals, each quarter. So the closed lost reason had to be selected by sales from list (competitor, poor customer fit, etc). Then the free text was a chance for sales to say what they thought was the reason. This was a helpful field to give sales the chance to put forward an opinion, but the structured reason data became a golden source of insight that drove future business and behaviour changes. Other information captured through that process included the driver of abandoning the deal (for example, pricing) and a sentiment analysis from very positive to very negative across a range of variables, such as relationship, cost, etc.

After this information was captured, the product team would review deals above a certain size and stage, and they’d document their own additional analysis and findings from the review.

Pipeline Management

In a growing company, successfully managing and forecasting sales can quickly become harder than looking at individual deals.

On a per deal basis, I’d learned how changing the conversation with customers created a more valuable dialogue and bigger deals, and I’d learned how to create a common language and objectives by improving my sales process, but as I’ve said, this only helped on a deal-by-deal basis. It didn’t help me understand my pipeline in full and as the business grew so did the number of sellers and deals in progress.

For some time, having good pipeline management still seemed to elude us, and by that I mean my leadership team and I did not feel connected to the heartbeat of what was happening on the ground in sales. We could pick out an individual deal, and if the opportunity was up to date, we’d have a clearer discussion about it than before. But if sales didn’t use our CRM pipeline management system consistently, then the shape of the pipeline wasn’t accurate. We didn’t know if we had enough opportunity, if it was progressing or stalling, or if it was going to close on time, late, or even at all. There was a missing link, and an important one at that. I needed to glue together the business’s need for a better understanding of our pipeline, a more accurate understanding of when our deals would close, along with the sales team’s single interest in winning more.

During chance conversation with an HR executive from another fast growing enterprise software company at a dinner I learned about the bumpy ride her company had been on through global expansion, and how as the team grew their results became unpredictable. It was hard to keep engaged with their growing sales team, which resulted in inaccurate forecasts and difficulty business planning. That had caused relationship problems with their investors. Not a good place to be.

They solved the problem by introducing two new behaviours championed by their executives and sales leaders.

Cadence and Coaching

I learned over dinner how a good sales cadence included a set of meetings that provided the missing glue. They approached these meetings as something that must help sales as much as help the business. She explained that pipeline calls so often add no value to sales, and they are little more than a frustrating chance for sales to be caught out for not keeping a system up to date. Her company invested in training managers to coach sellers, bringing helpful insights based on what was needed at different stages of the sales process. Managers had to be prepared to add real value with insight, time and resource commitments in those meetings. In return salespeople had to be prepared and ready to learn and to earn the right to get more help and resource from the business.

The rhythms of the sales meetings themselves were structured to create consistent interactions through the financial year, with clear mutual expectations between leadership, managers, and sales.

This was an eye-opener and made a lot of sense. We needed to focus on getting salespeople into genuinely useful, engaging conversations that would help them sell more, and then put guard rails around them so that those conversations could improve results and provide more pipeline transparency and accountability.

I remember that I wrote out on one page what I wanted to achieve through these two changes, cadence and coaching. On one page, I explained our cadence, which was a new regular set of sales meetings. It set out goals for sales managers on how they’d move from tripping up salespeople on missing details on their CRM records to coaching them through using questioning techniques to work out how to take a deal to the next stage.

Salespeople loved that they could earn more resources to help them win by engaging in the coaching process and showing up with well thought out data on their deals. We saw improvement in terms of the accuracy of our pipeline and forecast, which I loved too, because I was more confident planning ahead and reporting progress. Our sales win rate increased as well, as the sales team and their managers got more creative on how to win, and then reapplied their best insights back into other deals.

Our leadership team committed that we’d ensure that the full resources of the business would be brought to bear on those deals which showed promise through these meetings. We were intent that if salespeople were reluctant to embrace weekly scrutiny, they would happily accept help and resources and engage far more when the process offered them added value, helping them close more business.

Sales Coaching Techniques

Research has shown that sales coaching produces results. According to the Sales Management Association, companies that spent at least three hours per month coaching their salespeople through the steps of their sales pipeline had revenues an average of 11 per cent higher than those that didn’t.

Though managers often focused on coaching for late-stage opportunities or opportunities about to close, a better idea was to start with early-stage opportunities. There were two reasons for this.

First, coaching our salespeople on early-stage deals helped them weed out the unlikely and unqualified prospects and cultivate the right strategy for the qualified opportunities.

Second, the opportunities in which coaching had the greatest impact were those at an early-stage because deals were still malleable and had more time to influence the customer’s decision.

When facilitating a sales pipeline coaching session, a common mistake made by our sales managers was they focused on the past instead of coaching to the future. They would often ask salespeople to recite the events that have transpired up until that point in time, and then they’d tell the seller what to do next. This was managing, not coaching. Managing is about directing and telling people what to do, which leaves little opportunity for learning. In contrast, coaching is about education and empowering people to make the best choices in the future. Our change was to coach salespeople on how they were going to handle their calls with their customers or upcoming meetings and set a framework for making sound decisions.

The focus of the meetings we pushed for was less about quantity and reviewing every deal, and more about the quality of the coaching and making an impact. In our coaching sessions, we focused on a few deals but made sure we did a thorough analysis of them. Our mantra became, “Don’t skip over the details—that’s where deals are won and lost.”

Structuring Sales Cadence

When I write about sales cadence, the term is used to describe a recurring set of focused sales meetings with two objectives:

1. Ensuring pipeline health, measured by the stock of opportunities in the pipeline and their progression or flow through the sales stages.

2. Ensuring forecasting accuracy, measured by the quality of a forward-looking forecast on the value of deals won over a period of time.

Pipeline management responsibilities

Sales managers were expected to spend time each week in both one-on-ones with salespeople and in sales team meetings, receiving updates and providing coaching on deals, so that salespeople had the right help and support to move ahead. These meetings were sequenced into a rolling series of interchanging pipeline and forecast meetings.

We introduced one-on-one pipeline reviews. These started during the first week of a sales quarter and every second week thereafter, and each salesperson met one-on-one with their manager for a pipeline meeting. In this meeting they discussed their individual pipeline and might be asked about any opportunity that they were handling, no matter how new or how mature it was. During those meetings, time would be spent between understanding the summary and the detailed views.

The summary would include progress against target, stock of opportunities at each sales stage, and flow of opportunities through the sales stages. This established if the salesperson had sufficient deals in their pipeline to hit quota and whether they were progressing through the stages towards closure. This type of analysis led to discussions about balancing—that is, planning to prospect for more opportunities with business development versus sufficient time availability to cover the workload on the deals to keep them moving.

The detailed discussion revolved around looking at individual deals. The salesperson had to be ready to discuss key deals in their pipeline on the understanding that their manager could assist them and bring resources to bear. Preparedness demonstrated thought and attention to the work the salesperson had been hired to own. The sort of topics that got discussed included what had happened so far, then majoring on what were the next steps, what needed to happen to close the deal, and what were the anticipated timeline, obstacles, and actions. These were open questions to launch coaching discussions and allow for creative problem solving and support, as well as challenge the salesperson.

Being up to date meant using the opportunity record in the CRM system as a hub for information that could be used by sales and the supporting deal team to collaborate, with the goal of being competitive and winning. That meant capturing daily all-important progress, updates, actions, and next steps that were being managed.

The sales team would be expected to regularly revisit their opportunities, asking themselves a long list of questions and assessing what might have changed: If they were still happy with the close date, when were they expecting to receive signed contracts, ensuring the sales stage reflecting the current deal position, checking the next step, et cetera so that what the customer would buy and at what price remained clear, and the close plan was supported by the work to be done, agreed timetable and what was needed to get the deal closed.

Team Pipeline Meetings

In addition to individual, one-to-one meetings, starting from the first week of a sales quarter and every second week thereafter, a team pipeline meeting was held. This was at the end of the week following pipeline one-on-ones. This meeting was about mutual accountability and salespeople hearing other salespeople say what they were going to do.

Mutual accountability was a powerful dynamic in the team. These meetings had sales and sales management reporting to business leadership on pipeline health and key deals, and in return, leadership could commit to supporting critical sales activity with more resources.

The structure of the session was similar to the pipeline one-on-ones in the sense that it started with a summary review of the whole pipeline and key metrics and then took a deeper dive into the detail of particular deals in each salesperson’s pipeline, using the same open questioning and coaching style. We found that a wash-up between sales management and business leadership after the pipeline calls was the best way to decide upon resource allocation. We also used a minimum level of readiness to involve resources beyond the salesperson as being demonstration that an ROI analysis had been completed with the champion. This focused the early-stage deal activity and got it off on the right footing and showed qualification and engagement from the salesperson and the champion at the prospect.

Forecast Responsibilities

The second set of regular meetings were forecast reviews. The purpose of the forecast review was to estimate the opportunities likely to close in a given period of time.

Starting from the second week of a sales quarter and every second week thereafter, each salesperson would meet one-on-one with their manager, for a forecast review. But this time their focus was on forecasting what deals would close later that month and quarter. In this meeting they would discuss their individual quota for the quarter, and their orders signed so far in the month and quarter. Then there was a review of the pipeline focused only on that month and quarter. In this meeting, each salesperson would be prepared to discuss these specific opportunities set to close in the timeframe in detail. Once again, the conversation would use the elements of MEDDICC to understand and discuss the health of late-stage opportunities. The questions that needed to be answered included, “Why buy, why us, why now?” The manager and the salesperson would be intent upon creating an accurate forecasted sales number that could be communicated to the company leadership and used for business planning.

Team Forecast Meetings

There was also a team forecast review. Its purpose was to update sales colleagues and leadership on the estimated opportunities likely to close in a given period of time. This meeting was about mutual accountability and salespeople hearing other salespeople demonstrate what they were going to achieve. Mutual accountability provided a powerful dynamic as sales and sales management reported up to business leadership on what would be sold that quarter.

Measuring Performance

Measuring sales performance through the data captured in CRM proved to be a powerful tool when we struck the right balance of metric tracking, with not too many to confuse and not too few to miss key performance indicators (KPIs). We settled on some that were industry standard, easy to extract from our data, and insightful when looked at in terms of trends—year on year, fiscal period, or by territories, regions, teams, or individual salespeople, and also when studied with a filter on types of products sold.

The KPIs we tracked included:

Loss analysis. Using abandoned deals data, we could become more competitive in terms of what we sold and where, and also who was selling, using performance management as needed to address deviation below normal performance levels, thus raising overall performance of the business.

Conversion rate. Sales stage and opportunity value data helped us understand sales effectiveness and identify the size of the pipeline required to give sufficient coverage to meet expected sales performance.

Average duration at each sales stage. Using aging data from date stamps on the records, if deals got stuck at a stage for longer than the average, we could identify bottlenecks to focus on.

A more heuristic assessment was the average length of sales cycle through to win or loss. This was a helpful yardstick, though less useful as an isolated indicator because, though early stage deals were good, we’d engage in deals at varying levels of maturity and problem awareness.

Age of opportunity could be measured against expected sales cycle duration to predict whether it was likely to be won or lost.

Average deal value allowed us to identify key deals to target and prioritise resources, where the opportunity size exceeded the average.

Close date versus sales stage provided a view on whether the close date was realistic, based on where the deal was in the sales cycle.

Close date movements, or the number of times a close date for an opportunity was changed, provided an indication of ongoing qualification issues if a deal continued to get pushed back.

Stock of opportunities was the size of the open pipeline, measured as an amount and a count of the number of opportunities.

Flow of opportunities was the number of prospects moving between each stage, measured as an amount and a count of number of opportunities.

Forecast split out the pipeline for the quarter by forecast categories of “committed” (certain to close), “best case” (certain plus likely contingency deals) and “pipeline” (everything qualified and not omitted all together from the forecast).

Gap versus target used the amount of opportunity closed versus our predetermined target.

Coverage was a calculation of how many prospects needed to be in the pipeline to get us to the target number, based on current win rates.

Though technology choices to track selling are vast, starting simply, with reports that can be refreshed daily, gives most metrics a growing business need. Using advanced graphical representations and AI- driven predictions can be helpful only when the business and sales team are familiar with the simpler weights and measures described here that bring visibility and control to the sales motion. With those in place, it becomes easier and eventually second nature to get focused on the right opportunities and sales effort to drive business growth.

Final Thoughts:

In this note, I share insights from CloudSense's journey in building a sales-led culture that significantly enhanced our enterprise sales performance.

Key Takeaways:

Cultivate a Sales-Led Culture: Encourage all departments to prioritize customer needs and support the sales team's efforts, fostering a unified approach to delivering value.
Empower Sales as Customer Advocates: Recognise the sales team as a vital source of customer insights, guiding product development and business strategies to better meet market demands.
Hire Salespeople with Intensity: Seek individuals who are competitive, possess a strong work ethic, demonstrate curiosity, and are unafraid to pursue large opportunities, driving success in enterprise sales.
Ensure Organisational Flexibility: Be willing to adapt processes and solutions to accommodate customer needs, maintaining product integrity while enhancing customer satisfaction.
Promote Cross-Departmental Accountability: Regularly assess how each department contributes to enabling sales, ensuring alignment and collective responsibility for business growth.

By fostering a sales-led culture and building a team of driven, customer-focused sales professionals, startups can enhance their enterprise sales capabilities and achieve sustained success.

Richard Britton