Reconsider Pre-Sales at Scale

Startups transitioning to growth mode need to take a sober assessment of their sales motions as they lay the groundwork for a scaleable framework that will allow them to hit the revenue targets they promised their Series B investors. At this stage, there’s no longer room for organic instances of success. Instead, leaders of Sales and Solutions organizations need to perform a three-stage transformation that will create a professional sales machine capable of generating repeatable success akin to the sustained excellence of a top craft brewery:

1. Diagnose* - Identify what works well and what does not in these areas

1. Customers

2. Messaging

3. Methods

2. Mobilization - How should you take action to address your diagnoses? 

1. What resignations exist?

2. What’s your offer?

3. Establishing conditions of satisfaction

3. Sustaining Success

1. Being accountable

2. Sharing results, good and bad

3. Being ready to do it all over again

In my experience scaling the Pre-Sales practices at CloudFactory, tooling assignments played an outsized role in Pre-Sales. So, I will focus on that area to provide a detailed example of the three stages of transformation.  

Diagnoses

While my diagnosis had many facets, I’ll discuss the conventional wisdom adopted as “truth” when I joined the team: being “tooling agnostic” was a competitive advantage. In actuality, I found many disadvantages that I attributed to the tooling agnostic approach:  

• Each prospect was subjected to an exhaustive Discovery process that often stretched for 2, 3, or more meetings as Solutions tried to identify the “Perfect Tool” for each use case. 

• A perceived lack of expertise - working with so many tools robbed the team of the opportunity to build expertise in any one tool, leading to many instances of learning on the fly in full view of the customer.

• Without standardized tooling, each engagement required customization. There were no standardized contracts, tooling configurations, data formats, or onboarding protocols. The company had to be ready for anything as a “Tooling Agnostic” service provider. My assessment:  When a company must be ready for anything, it can prepare for nothing. 

When a company must be ready for anything, it can prepare for nothing. 

Mobilization

A significant change in approach was warranted. We would sunset the Tooling Agnostic approach and instead invest in developing expertise in a select group of tools. Over the next quarter, we would retire the old message and adopt a new one. 

The Old Message: “We can work with any tool.”

Subtext: ”There’s really nothing special about the services we provide. So, we can deliver them using any old tool.”

The New Message: “We work only with best-in-class tools.”

Subtext: “We’re experts at what we do, and we’ve chosen the best tools to work with.” 

I understood that the team was heavily invested in the Tooling Agnostic approach and decided to proceed carefully. Rather than roll this out as a significant initiative, I incorporated many aspects of our new approach into our daily course of business with little fanfare. I intended to allow the entire organization to become so familiar with the individual facets of the new approach that its eventual rollout would be greeted with a shoulder shrug rather than outrage. A few examples of these incrementation changes were as follows:

• I spoke constantly of our in-house expertise and promoted the virtues of each of our chosen tooling solutions. 

• I negotiated discounted rates with our preferred tooling providers and championed the competitive advantages they brought to us.

• My team shifted from a “Tooling Discovery” posture in Pre-Sales, where they searched for the right tool, to a “Use Case Optimization” posture, where pre-determined according to the use case and instead worked with the client to prepare them for a successful outcome.
  

Within the span of a quarter, we had increased our deal velocity and improved our close rate. We set a record that quarter for the number of AEs at quota. In post-sales, we experienced improved outcomes due to shortening our onboarding ramp and improved client satisfaction. 

Sustaining Success

When creating a new Pre-Sales process, building your new program with sustainability in mind is essential. Your Pre-Sales organization needs to maintain its edge by constantly monitoring its performance while considering the impact of internal and external changes. 

Our Solutions team instituted three practices that afforded us a regular chance to consider our past performance while sharing knowledge about business and technology;

1. Solutions Knowledge Sharing Sessions: Bi-weekly sessions that periodically included Product, Operations, and Client Success teams

2. Tooling Vendor QBRs: These two-way sessions emphasized feature development and operational performance. 

3. Sales/Solutions Syncs: Monthly discussions with sales leaders to discuss trends and high-value deals.

My team of Solutions Professionals embraced their roles as tooling experts. Our new Pre-Sales practices put us in a position of sustainable strength, where we were constantly learning, adjusting, and improving our performance.

*My appropriation of the terms “Diagnosis” and “Mobilization” have been inspired by the writings of Chauncey Bell.

Discovery: Discovering Rewards (and Risks)

The Discovery stage of Pre-Sales, as the name would imply, is an opportunity to discover possibilities. Having validated an Opportunity, this is the stage in which Sales and Solutions get to work—rolling up their sleeves to explore the prospect’s identified needs and then document them and their associated goals, constraints, and risks. However, when you work in an innovation field, such as AI, the exploration doesn’t stop there. It’s the role of a Solutions professional to examine the prospect’s use case and continue to ask questions in an attempt to uncover additional value that the prospect hasn’t previously considered.

It’s possible to further the Discovery conversation beyond requirements gathering into a new, more enriching path that can create attractive new options for the customer to consider

A customer prospect enters Discovery conversations with expert-level knowledge of their own use case. However, their presentation of requirements is limited by their knowledge of what the selling organization offers. prospects may be unaware of the latest features. Or worse, they may misinterpret the capabilities of the selling team, which can lead them down the path to a dead-end outcome. Even if the prospect is spot-on in their understanding of the published offering from the seller, they cannot possibly be aware of the lessons learned by the selling team in recent months, weeks, or even days in some cases.

When there’s a gap between the prospect’s understanding of the offering and the full breadth of the solution’s possibility, it’s a Solutions professional’s job to identify and then reconcile that gap in understanding with utmost care. Prospects have little appetite for a brain dump by the Solutions team. By uncovering and exploring a prospect’s gap in understanding with curiosity and care, it’s possible to further the Discovery conversation beyond requirements gathering into a new, more enriching path that can create attractive new options for the customer to consider.

There is another side of the Discovery process to consider, and that’s its role in identifying risks. The risks I’m talking about are more nuanced than those that would surface as part of the validation process (e.g., budget, timing, etc.) The risks that a Solutions professional can uncover require greater understanding, such as definitions of quality acceptance criteria or data cleanliness or even such broad areas as regulatory compliance or systems architecture. In all these examples, the knowledge, awareness, and curiosity of the Solutions Pro all play into surfacing potential vulnerabilities in these critical areas.

Once such risk factors are identified, they can be considered by Sales management (i.e., is this a deal-breaker?) and mitigated (i.e., can we resolve it in pre-sales or mention it in the contract for resolution post-sales?) Most importantly, each risk identified during Discovery is one less issue that might surface later in the customer journey, putting the deal or the customer at risk of churn.

In a future post, I will go into greater depth as to how my teams utilize organizational knowledge sharing to inform their Discovery questions and track their impact on pre-sales effectiveness.

Keep Demos On Target

If you nail a demo, you can light up a prospect's imagination with countless ideas of what might be possible. However, it’s waaaaay too easy for a poorly executed (or poorly timed) demo to shut down a prospect’s interest and instead “inspire” an early end to your meeting and to your opportunity for a sale. 

In my experience, there are three must-have elements in a good demo:

1. Make it Engaging - Whether on a stage, in a conference room, or on a screen, the presenter should adhere to the basics of good public speaking, keep a good flow, and bring the audience along with them from start to finish. 

2. Nail the Execution - Practice, practice, practice. Limit live content to speaking only wherever possible. No Typing. No page loads. No progress bars.

3. Keep it Relevant - Your demo should be 100% relevant to the prospect conversation at that moment in time. Incorporate your customer’s use cases, data, demo scenarios, logos, and anything else you can acquire from them into the demo. Bloat your demos at your own risk*.

When I arrived at CloudFactory, the standard practice for demos was to delay the demo until the prospect’s use case had been validated, the use case had been reviewed, samples of client assets (e.g., data for annotation or documents for processing) had been provided by the prospect, and the team had specified and tested the desired tooling for the use case. Then, and only then, would the team conduct a demo.  However, I made an assessment that this approach was not appropriate in most cases. 

After watching countless hours of recorded Zoom calls and talking with members of the team, I made the following assessments:

• Early presentations were lacking in depth and detail. Discovery calls covered high-level subjects (company mission, operating structure, history, etc.) but lacked the kind of detail that could give a prospect confidence in our ability to do the work.

• Prospects were frustrated. Whenever prospects asked questions attempting to satisfy their desire for expertise, the teams would give them the “stiff arm” treatment, resisting specifics until they were ready to demo. 

• Dragging out Presales: Collecting the data and use case details needed to conduct the desired demo added precious time and confusion to the presales process. In many cases, the prospects’ frustration would cause them to disengage quietly or simply sign with the competition. Those who endured the presales journey long enough to see a demo were often delighted with the results. But they had to “earn” their delight by enduring our lengthy presales process. 

To address the pain detailed in my assessment while keeping sales efficiency in mind, I devised a new demo process that reconsidered the structure and timing of prospect demos. We created three different demo scenarios, each crafted appropriately for the stage of the opportunity. 

Demo 1: Discovery Demo

Objective: Demonstrate our expertise for the use case in question. I.e., “We’ve done this before.”

Parameters: A brief, pre-recorded walkthrough(5 minutes or less) of a similar use case using open-source data.
Desired outcome: Address early client questions, win their confidence, and ensure they stick around long enough for us to conduct a full demo later. 

Demo 2: Pre-Proposal Demo (Optional)

Objective: For complex use cases, walk through the intended solution with the client.

Parameters: Ask clarifying questions and validate assumptions before pursuing the analysis necessary to prepare a proposal. 

Desired outcome: Improve confidence and technical buy-in before committing to a proposal. 

Demo 3: Proposal Demo

Objective: A full demo to complement the written proposal. 

Parameters: The demo should include client assets, specified tooling and end-to-end solutions architecture. 

Desired Outcome: Win the business.

*Note there is an opportunity to consider here for senior sellers who consider themselves ambassadors of possibility. You might elect to tantalize your prospect with a taste of something they had not yet considered. But this is a master move, not to be taken lightly. Pursue this path only if you have the highest confidence that your prospect will find it relevant, valuable, and exciting. Otherwise, stick to the 100% relevance approach.

From Home Brewer to Craft Brewery

Scaling a company’s solutions strategy requires a hard look at the Pre-Sales journey. Taking my inspiration from The Lean Startup, I wanted to examine the existing process and make the adaptations necessary to progress the Pre-Sales journey from an uneven series of hits and misses toward a continuously improving process with repeatable success. As anyone who has choked on a glass of skunky home brew knows, your experience at the local microbrewery is much more likely to deliver a pleasurable pour, visit after visit. 

During my first 90 days at CloudFactory, I conducted a listening tour around the company to orient myself as the leader of the new Solutions team.  When talking with leaders from Go-to-Market and Delivery, I identified three areas in the Pre-Sales journey with drastic inconsistencies that created complexity and raised churn risk. 

These three areas offered a fantastic opportunity to improve the Pre-Sales experience for our clients and a smoother operational flow for our teams in Pre-Sales, Post-Sales, and Delivery:

1. Demos - Existing sales practices discouraged any demos until the AE had validated the opportunity. Further, sales would only offer a demo once we had received a sample of client data and our team had analyzed the data. 

   Impact: Clients experienced a weeks-long validation process without being afforded an opportunity to learn about our methodologies or experience our expertise. 

2. Discovery - There was no step in Pre-Sales where our inconsistent utilization of Solutions Consultants was more consequential than in Client Discovery. Incomplete exploration of client opportunities left our team struggling to catch up with the necessary for defining the use case, business case, and conditions of client satisfaction.  Such details were gathered much later in Pre-Sales, if at all.

   Impact: Insufficient client discovery reduced our close rate. For deals we were fortunate enough to close, the missing details led to extended onboarding, poor Delivery performance, and palpable client frustration.

3. Tooling Assignments - The company had embraced its “Tooling Agnostic” approach quite literally. In practice, every Opportunity started from Square One. Any tooling option was on the table. We conducted a Tooling Discovery for each and every Opportunity that involved additional meetings and detailed Q&A in search of “The Perfect Tool.”

   Impact: Unlike our competitors, we subjected prospective clients to an exhaustive search process. The added discovery steps slowed down our deal velocity and reflected poorly on our sales teams, as clients interpreted our tooling exploration as an indication of our inexperience.

In my next three posts, I will detail my approach to overhauling our approach to Demos, Discovery, and Tooling Assignments.

Making Solutions a Habit

Making Solutions a Habit for the Sales Team

When I first accepted the role to build and lead a new Solutions team at CloudFactory, I knew I was joining an organization that had experienced significant success. I also knew the selling process that had taken them thus far would not scale to support the following growth milestones they hoped to achieve. 

My early assessments were as follows: 

1. Solutions involvement was uneven across the sales team. The single determining factor for a Solutions Consultant’s participation in a deal was their relationship with the Account Executive rather than the Solutions requirements of the given Opportunity. 

2. Sales had grown accustomed to following an “Organic” sales process, with only one common thread: close inbound leads as quickly as possible, which induced a behavior that I like to call a “Rush to Sign” (RTS).  

3. The consequences of RTS included incomplete client Discovery, incomplete success criteria, and inconsistent Solutions Architecture from deal to deal. 

My approach to address the assessed condition and put us on a scalable path was to pursue three main objectives.

1. Normalize the Sales-Solutions Relationship - i.e., Make Solutions a Habit

2. Define the roles and responsibilities within the PreSales Journey

3. Apply targeted standardization within the Pre-sales process. 

Making Solutions a Habit

There were three different levels of experience among the AE team, and each of these groups approached their relationship with the Solutions team in their own way. 

• The Grizzled Veterans had been around the company for a while and had each figured out a formula for sales success. To this group, Solutions Consultants added complexity and friction to their deals. They would avoid working with an SC whenever possible. 

• The Noobs had a year or two of experience in the AE role and relied heavily on the guidance of their manager and the Grizzled Veterans. Noobs had no idea who SCs were or what they did. Their interpretation was that SCs were a threat that they should avoid. 

• The New Seniors were recent hires who had been around the block a while and knew the benefits of working with SCs from past companies. The New Seniors worked with SCs whenever possible. 

My goal for normalization was to eclipse the prevailing thought that Solutions Consultant involvement was a matter of choice with a new concept: SCs were copilots for the Account Executives' deals. 

I employed a carrot-and-stick approach to achieve this normalization.

• Carrot: Document wins from the New Seniors, then use their testimonials to highlight the benefits of working with SCs.

• Stick: Actively monitor the Opportunity Pipeline for high-value opportunities without SC involvement. Engage the AEs manager to “encourage” SC engagement. Note: None of these steps are possible without Sales Leadership's full partnership and involvement. 

• Carrot: I became a fixture at Sales team meetings to share lessons learned, invite questions, and address concerns in the open for all to hear. 

• Stick: Working with RevOps, we set a rule in Salesforce that prevented qualifying Opportunities from advancing past validation without an SC assigned to the Opportunity. Note: Some AEs would game this rule (SHOCKER!), so continued vigilance in pipeline monitoring was necessary.

• Carrot: Dealwire announcements were updated to include recognition of the SC involved in all wins. I would actively monitor and comment on these wins, pointing out value added or obstacles addressed contributing to the ultimate success. 

• Stick: This stick was for my team. We promised to do no harm; i.e., we would not slow things down. Working with RevOps, we started tracking various aspects of “Close Velocity”(e.g., Time for Validation) to hold ourselves accountable to our promise. 

The results from these changes were phenomenal. Within a single quarter, the SC utilization quadrupled (as measured in both the Number of Opportunities and Pipeline MRR$), setting the stage for a record sales performance in the following quarter.

Establishing Accountability: Promoting and Fulfilling the Mission

In my last post, I walked through my process for establishing the mission for my new Solutions team. However, as anyone who has worked in an organization that failed to “walk the talk” of their mission statement knows, a mission statement is meaningless without concrete actions to substantiate it. 

If you declare a mission statement in the forest, does it get lost in the brush? 

Substantiation of our new mission statement required three steps:

Step 1: Promote the New Mission Internally

It was critical to post the new Mission Statement in highly visible ways. These included an internal blog post, a new opening slide for all internal decks, and adding it to the onboarding curriculum for new hires. 

Step 2: Ensure the team owns the new mission

I wanted my team to understand how seriously we would take the new mission statement.  I introduced the mission during our internal sync. My presentation included a summary of what I heard during my listening tour. We unpacked and discussed each takeaway and how our mission addressed the lessons learned from the listening tour.  Later on, I revisited the discussion during 1:1’s. The mission statement would then become a mantra that I repeated whenever there was a question about a request that had come our way, i.e., “HOW do we respond here as the owners of the company’s technical relationship with this client?”

Step 3: Declare your accountability

Our internal constituents needed to understand how the new mission would inform my Solutions team’s work with them. Achieving such understanding was necessary for the mission to gain traction truly. Each of our three constituent teams needed to hear the a reinterpretation of our mission as it pertained to their worlds. The most prevalent concern I heard on the listening tour was the uncertainty surrounding when to engage the Solutions team. My ultimate goal for each group was to remove the uncertainty once and for all.  The interpretation for each group was as follows:

• For Sales: Solutions is your partner for EVERY opportunity. 

• For Client Success: Solutions is your first stop for any technical questions with clients.

• For Delivery/Operations: Solutions owns technical implementations. 

I recognized that positioning my team in this way would expose us to many requests that were not our responsibility, e.g., No, Solutions cannot help with HIPAA compliance, or Sorry, we can’t set up that virtual workstation. However, the effort required to triage, and then redirect such requests was minimal. More importantly, we were involved in many more client engagements than in months past. And that added exposure was the gold at the end of the rainbow for my Solutions team. Within a couple of months, Solutions partnerships became a standard feature at our company, and people embraced them as it they had been in place since Day 1.

Define the Mission for the Team

As a new leader of a new Solutions organization joining a company experiencing rapid growth, I prioritized getting oriented with the people I’d be working with and the culture in which we would work together. It was time for a listening tour to explore three main questions:

1. What’s the view from up top?

2. What are the needs and expectations of our clients? 

3. What are the concerns of the team and their colleagues?

What’s the view from up top?

When coming out of the gate, it’s essential to ensure that you have a mutual understanding with senior leadership about what they expect from the Solutions organization. Notes from my interview cycle provided the background necessary to complete this process promptly. 

• What are the OKRs for the current FY? - First and foremost, these need to be In the background when defining the team’s mission. While it’s not necessary to address OKRs head-on with the mission statement, you certainly don’t want there to be a conflict. 

• What are their aspirations for the company in the marketplace? - Exploring this question with leaders may uncover new observations that had not been previously brought to the forefront. 

• Where are the pains or concerns internally?  - Whether or not they see a direct correlation between Solutions and those aspirations, such concerns are essential to know about. Solutions is such a critical function with amazing relevance throughout a technology organization that I consider anything fair game when considering Solutions as having a meaningful impact anywhere along the customer value chain. For example, are there operational headaches associated with onboarding new clients that Solutions can flag early in Discovery? 

What are the needs and expectations of our clients?

When exploring this question, I feel it’s crucial for a Solutions Leader to get a 360-degree view AND to apply the unique “Solutions Lens” to that view. In one case, I learned that a premium client had been expending significant resources transforming data we were delivering to them that we considered “complete.”  The additional work was quite a burden on our client, and exposed us to an unnecessary churn risk had we not revisited the acceptance criteria with them.

Get a complete view of the client experience by interviewing:

• Sales

• Customer Success

• Operations

• Support

• Clients (either directly or by reviewing call recordings.) 

What are the concerns of the team and their colleagues?

Here, you are looking to establish mutual conditions of satisfaction between the Solutions Team and their various partners in the organizations. 

• For Pre-Sales - 

• What do sellers feel they need to succeed in closing deals? - Are Pre-sales team members working with common goals in mind?

• Are they familiar with the Pre-Sales function? - Take nothing for granted. Inexperienced salespeople can perceive Solutions partners as threats that are reluctant to engage. 

• Are Pre-sales pros being misused? - Competent Solutions Consultants are amazingly talented, which can sometimes lead to others tasking them with responsibilities extending into Post-sales Sales or even Product Development or Support. 

• For Post-Sales

• Are they set up for success? - Have Statements of Work, handover documents, and client assets been prepared with Post-sales success in mind? 

• Are they appropriately positioned in the customer journey? - Insulating Post-sales engineers from Pre-sales conversations can lead to sluggish delivery and delayed revenue realization. 

• Is there sufficient coordination in Post-Sales? Project Management neglect lurks in the background for organizations experiencing rapid growth. 

Putting it All Together

With the listening tour complete, I had a good sense of the misalignments that existed between the team’s self-perceived responsibilities and where our organization and clients needed us to be, which gave me the guidance I needed to establish our mission; CTS is the owner of the technical relationships with CloudFactory clients. 

I shared the team’s mission widely in formal and informal settings and referred to it often in meetings as a touchstone to validate questions and requests. Within a quarter, the confusion around the teams’ place within the company had vanished, and we were ready to begin building our Solutions Practice for future success.

Designing a New Solutions Practice

Today, I begin a series of posts to reflect on my time at CloudFactory as Director of Client Technology Solutions (CTS.) This first post will describe the state of my organization when I joined in 2021 and the three initial objectives that I addressed in my first 90 days on the job.  The post will also provide a preview of other topics that I will cover in more depth in subsequent posts. 

When I joined CloudFactory, the company was growing rapidly, and the sales pipeline was brimming with opportunities for the company’s data annotation services for AI teams. My team included Solutions Consultants, providing presales support to the Sales team, and Enablement Engineers, who provided post-sales engineering support for newly signed and existing clients. While the individual pre and post-sales roles had existed at the company for a few years, the idea of teaming them together in CTS was new, and that presented us with several challenges: 

1. Very few people at the company knew what we did.

2. Those who knew individual team members didn’t know how to engage them.

3. The team members themselves didn’t know how to work with each other.

My first objective was to define the mission for the team and then orient the team members and the rest of the company around that mission. 

While the first objective was foundational, my second objective was forward-looking. We needed to implement a scalable, solutions sales methodology. Until then, each account executive had used their own approach to selling based on a common set of resources provided to them. Predictably, this led to a variety of deal structures with massive inefficiencies in pre-sales and post-sales. Each signed deal included a unique architecture, unique deal terms, and plenty of open questions. 

The third and final objective was to reign in our tooling assignment process. Tooling was a mess that needed cleaning up fast. I speak of the labeling software solutions (aka “tooling”) that our CloudWorkers used to deliver our data annotation services. While our competitors went to market with their own tools, CloudFactory chose to be “tool agnostic” in its approach. Opting instead to use third-party tools, which, theoretically, allowed us to find the “right tool” for each job while relieving us of the costs associated with building and maintaining proprietary software. While this approach made sense in isolation, when applied at scale, it created massive inefficiencies that lengthened the Discovery process needed to define the client’s deliverables and hampered our ability to build expertise in our annotation practices.

So, for the third objective, we needed to create a  new tooling approach that allowed the flexibility we desired but also included a level of standardization that allowed us to speed up the tool assignment process.

I'm proud to say that over the first 90 days of my time, we made significant progress and set up the company for improved sales success within the first six months of my time there. 

In subsequent posts, I will write more extensively about each of the three objectives, providing greater detail on my plan for achieving each of the 90-Day objectives, along with additional lessons I learned during that ramp-up period.

Please join me on this journey as I discuss the diagnosis, design, and mobilization necessary to build a new Solutions Practice at CloudFactory.

Are You Listening?

Are you Listening?

You and your colleague, Bryn are meeting with a potential customer. With little prompting the customer, Seth, goes on at length about his organization, its objectives and challenges. You follow Seth’s lead and ask questions that allow you to drill down into pain points as you attempt to tease out the critical details. This isn’t the way you had anticipated the meeting was going to go, but you recognize the situation for what it is; a Golden Opportunity!

Your colleague Bryn, meanwhile, is impatient to “get started”, to get her turn to speak. She’s interjecting with comments rather asking than questions.

You scratch your head and wonder to yourself about your colleague; “is she even listening to what’s being said?” Bryn obviously doesn’t recognize the value what Seth is offering. She doesn’t realize how many of your pre-meeting assumptions are being refuted and more importantly how many new possibilities Seth is opening up with each new tidbit shared.

Bryn’s on a Powerpoint freight train, determined to be heard. You have no choice but to throw yourself on the tracks. Stop that speeding train before it demolishes the opportunity that you see on the horizon!