Enterprise Client Acquisition: Chris Falk Of Skrillo On 5 Steps to Winning and Keeping Major Clients
…Account management — Whether it is account management of customer success, this is going to be the defining factor in retaining that client. Problems will happen as that is part of business. Your team needs to maintain the same level of encouragement they had before the client was won. A proper account management plan includes a cadence that is agreed upon by the customer as well as spontaneous check ins. It will also include foreshadowing efforts surrounding upcoming changes to service, contract renewals, price increases, change in contacts within the company and the company’s future plans for expansion and growth. You should be setting touch points on the calendar as well as pre-scheduling notes within your CRM…
Securing and retaining enterprise clients is a major milestone for many companies, yet it requires a distinct approach, strategy, and mindset. From the first pitch to long-term account management, what does it really take to win over, and keep, major clients? What are the common pitfalls to avoid, and what strategies have proven effective time and again? In this interview series, we are talking to B2B sales leaders, enterprise account executives, founders, consultants, and anyone with experience in enterprise client acquisition about “Enterprise Client Acquisition: 5 Steps to Winning and Keeping Major Clients.” As part of this series, we had the pleasure of interviewing Chris Falk.
Chris Falk is the founder and principal consultant of Skrillo, a revenue performance firm specializing in execution-first consulting methodologies. Chris began his career in high-volume sales roles and progressed through the ranks to entrepreneurship, personally closing more than $150 million in enterprise deals while supporting teams responsible for an additional $500 million in revenue across sectors including SaaS, technology, and manufacturing. His operator-led approach stems from personally navigating enterprise deals and guiding teams through complex sales cycles, enabling him to bridge the gap between strategic recommendations and real-world execution that traditional consulting firms struggle with. Chris believes in an execution-first methodology, delivering measurable results in compressed timeframes. His approach integrates directly with client leadership teams and employs market indexing and buyer receptivity analysis to design territories around high-probability prospects. Chris serves clients globally across multiple industries including technology, manufacturing, energy, and commercial services. His work has gained industry recognition as representing broader trends toward accountability-driven consulting.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Appreciate the opportunity to speak with you. Honestly, getting to where I am now happened so naturally. I started in high volume call center sales when I was a teenager and something about being able to interact with multiple people daily was exciting for me. While I stayed doing that for a while, I eventually had stint working in the oil field for a year and half until I realized that I much preferred the commercial side of the economy. I took an entry level sales job at an industrial products company and quickly moved up the ranks to Business Development Manager, then to a larger company then into private equity backed roll up. I had a good reputation for being able to deliver results quickly, so I had people from within the industry asking me to moonlight to support their businesses and thing just kind of transpired from there.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
While the list is long here, I did have a situation where I was working on a 7-figure deal with an energy major when I was younger. It was my first time handling a contract that included a dozen stakeholders, and the Director had a name similar to Gary Busey. He event looked like him a bit. So right from go I messed up his name and no one thought it was a good idea to correct me. As the deal progressed, we had a bit of a snag on our end of things, and I pulled the amateur move of making up a story. I figured because so many people were involved from their end I could get through it. Well, the truth ends up coming out and “Gary Busey” ends up walking into my office. So, I greet him, he closes the door, sits down and says, “My name isn’t Gary Busey”. While I felt like a fool, what he said next was a lesson that stuck with me. He said “Mistakes happen. We are one of the largest energy companies in North America, we can fix mistakes. But people need to be up front about them. You aren’t going to lose our business over this, but if it is a pattern we will have no choice but to find someone else that can serve our commercial interests”. Ever since that impromptu meeting I have never make up a story in a business setting again.
What do you think makes your company stand out? Can you share a story?
I’d like to say our personalities but that’s arguable to some. What we have found after working on larger projects for clients is that we are execution focused. While a consultant is a consultant to most, because of our background as operators we end up integrating with our clients to the point of being able to blend in. for example, we had a client that was in a pinch as they had been scheduled to keynote as one of the largest industry events in their space. They gave me a last-minute call and said, “We are in a bind. Do you think you could go?” Two weeks later I am standing on stage delivering a keynote about their solution and position in the industry.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.
One of the hardest decisions I had to make recently was to exit a partnership. While the situation was profitable and I was able to leverage my background in the space, there were signs that the long-term outcomes would weigh negative against us. The hardest part was that we put off steady project-based work to pursue this so by walking away meant there would be some rebuilding that would need to take place. Ultimately it was the right decision for us as we have been able to stick to the vision and stay within our lane that we could go fastest in. One of the key take aways from situations like this is that you need to stay true to the vision and more importantly, be able to communicate that vision clearly.
Thank you for all that. Let’s now turn to the focus of our discussion about Enterprise Client Acquisition. In order to make sure that we are all on the same page, let’s begin with a simple definition. What does Enterprise Client Acquisition mean to you?
Enterprise client acquisition is organizational relationships with contracts. Like all relationships there is a give and take. There needs to be a mutual beneficial dynamic on an operating level which is why most enterprise sales organizations are 80% systematic and 20% gray area. While the process and approach can be a bit rigid, the relationship development requires a bit of letting your hair down. Especially for long term contracts. The number of hours teams from both organizations will spend with each other is going to surface interpersonal dynamics that can make or break a relationship.
What are the first actions to take when approaching a potential enterprise client?
Understand what you are trying to get into. By that I mean, survey the situation. If the company is publicly traded it’s quite easy to find information on what they are currently doing and how they do, but you want to go further than this. Initial conversations need to be light and focused on fact finding. Who are the key decision makers, how do they make decisions, how do they operate their budgets, have they implemented procurement systems or use any type of internal methodologies, who are they working with, basically anything you can uncover will help you to not only understand what challenges you are going to be up against and more importantly, are they the right client for you. We had one client recently that came to us after landing a supermajor as it almost crippled their business. All because they weren’t prepared for the amount of work and commercial structure it would take to serve them.
Which level of the organization do you reach out to when approaching a potential enterprise client?
This depends on a few things. What are you trying to sell them and what does their organizational structure look like. There are many enterprise organizations that operate like a cluster of smaller organizations where Directors and regional managers have a lot of internal pull. There are others that follow a top-down org chart with clearly defined roles and responsibilities when it comes to procurement. When it comes to the product or service, the organizational structure is going to be key in defining your starting point. In the case of not having a clear picture on the company, you typically want to start one or two levels below who would be the actual decision maker. The staff at this level are going to have a lot of information they can share and will likely be users of your product. If they are in a top-down organization, it is also likely a VP or Director will delegate discoveries downward. That’s where you can find your champions easily.
What is the best medium to use to ask for a meeting? Cold call? Linked-In, Email? In person? Can you please explain?
In person is ideal, but usually the phone is where most conversations start. Gone are the days of being able to walk into an office tower freely and knock on doors. Since RTO has been ramping up, more people are at their desks and readily available to answer their company phones. Email does work but with the way technology has taken over, most IT teams have implemented strict spam blockers that filter out nearly everything that isn’t internal. I personally believe in the omni channel approach. This is using all mediums available. If they don’t pick up the phone or return your voicemail, send them an email. If they don’t return the email, send them a LinkedIn message. If they don’t respond to that, find the industry event they are going to be at. Never forget to use referrals either. In most industries, the people at the top move from company to company so their networks are large. Leveraging current relationships can go a long way when other channels aren’t working. Going back though, the phones are winning in the outreach channel wars for those that can’t be in person.
What are the most common mistakes companies make in pitching to or onboarding with an enterprise client?
One we see often is failure to position yourself as someone in the industry. A VP at a chemical company is more likely to make time to listen to someone that is involved with chemicals. We do an exercise around this called Peer Positioning which essentially refines first stage outreach communication to sound more natural to the prospect. Like you are supposed to be there. Another common mistake is presenting yourself with a lack of commercial acumen. Enterprise deals require a lot of moving parts, and no one knows this better that the people procuring products and services within enterprise. Too many first pitches and onboarding attempts fail when the enterprise client realizes you don’t understand the commercial structure. No one wants to do more work, and if you are unable to carry your own weight, the customers won’t carry it for you.
Can you please walk us through one enterprise win from first outreach to renewal. What were the turning points, and why did they work?
I’ll try to keep this brief. We found a customer that was doing just over $44B in annual revenue that had lofty goals for expansion. In order to achieve their goals, they would need to improve existing infrastructure to be able to expand operations. With the information we had our first stage of outreach allowed us to position ourselves and being somewhere in the know. Typical approach would have been to find facts, but for 3 months we engaged in an exchange surrounding planning and deployment challenges. From here we were able to circle the organization to loop in additional stakeholders and influencers. The turning point here was that we had pre-existing knowledge, we bagna with relationship development, once that relationship was exhausted, we were able to create internal social credit to move up the ranks and across the org. From there the goal was to deliver a series of tailored presentation to the different stakeholder groups. After the presentations we found out that one group was blocking us due to a pre-existing relationship they had with a competitor. The goal from here now was to build a long-term business case that would carry more weight that a single stakeholder. Through that we were able to participate in a design study which further cemented our position inside of the org. At this stage we brought our technical team in and managed the relationship development around the idea of what it would look like if we were your service provider. The project eventually stalled due to budget. So, we maintained contact and kept up with changes in the organization. Once the project came back off the shelf, we capitalized on the time lost internally and supported their project scope and specification design. We were awarded the initial contract as a sole source. Even though we were awarded the contract at this stage, the selling didn’t stop there. We remained present both on the front line and back end for the duration of the project to ensure a continuation after completion.
There were a lot of moving parts here, but this is similar to most contracts of this size.
Enterprise buys as a committee. How do you map stakeholders, create an internal champion, and equip them to sell your solution inside their org?
Relationship development. To understand the inner workings of a company you need to ask the right questions and build towards a relationship. We use a custom-built graphic for org charts with associated roles, sentiments and positions attached to each stakeholder. Our goal is to find the loose end and try to tighten it up as quickly as possible. Internal champions are created on their belief that something needs to change and that they can support that change. While it doesn’t sound pleasant, a lot of stakeholders are trying to navigate internal politics and, in some cases, move up the ladder. If they believe you can help them do this, they will go to the end of the earth to implement your solution. Converting them to an evangelist is sometimes easy but having them convey the right message is where it takes some work. Quite a bit of time needs to be spent with them to help them understand how your solution affects each department that will be involved.
Here is the primary question of our discussion. Based on your experience and success, please give us your five-step playbook for winning and keeping an enterprise client. Be specific about actions, tools, and owners for each step.
1 . Survey the customer — Go deep in research and early conversations to uncover as much information on the organization. You want to know the people, their purpose, their beliefs and the processes they need to adhere to. The starting point for this is going to be mid-level managers as they are likely to be to most interactive and have their own internal ideas of how things in the organization should be done. The information here is going to be the foundation for every step after this.
2 . Create an account plan — From the information you have gathered during your survey stage, you want to construct a detailed account plan that will include all stakeholders, stakeholder sentiment, current initiatives, legal process, vendor onboarding procedures, security compliance, financial barriers, current vendors, deployment abilities and any timelines available. You can build a simple spread sheet, mermaid chart or CRM. Make sure that the details are readily available across your team and organized for context and next best actions.
3 . Form a business case with your presentations — Most buying committees have some version of size of prize exercises internally. These can be complex for them to go through, so it is important that you are presenting not only the solution and how it benefits them, but also the supplying them with the commercial details and downstream outcomes from implementing your solution. Most enterprise companies are pulling data from their ERP and using spread sheets for these exercises. It is ideal if you have a calculator build in Excel that is a guided way for the committee to input the data and receive an immediate output.
4 . Establish a path forward framework — People love predictable, and businesses are no different. When you are facing contracting you need to have a path forward clearly defined that can be mutually agreed upon or jointly built. Once you have a champion it is likely they became a champion as they will be interacting with your solution on a regular basis. Leverage this relationship to define what first stage will look like to the customer and extend this into the renewal stage. This is going to help them with forward planning and more importantly set the stage for a continuation that is far easier for them to commit to than go somewhere else.
5 . Account management — Whether it is account management of customer success, this is going to be the defining factor in retaining that client. Problems will happen as that is part of business. Your team needs to maintain the same level of encouragement they had before the client was won. A proper account management plan includes a cadence that is agreed upon by the customer as well as spontaneous check ins. It will also include foreshadowing efforts surrounding upcoming changes to service, contract renewals, price increases, change in contacts within the company and the company’s future plans for expansion and growth. You should be setting touch points on the calendar as well as pre-scheduling notes within your CRM.
What systems or processes are essential for keeping enterprise clients happy?
Nothing beats a transparent account management plan. You don’t want to share all your internal details with customers but giving them visibility in what the coming weeks, months and even year look like helps to build trust and maintain the relationship that was started. Account managers and Customer Success should be communicating this upfront with customers. What we typically create within the account plan is an SOP for account management with notes from other departments to be included in CRM entries. This is going to help you company maintain visibility should there be any staff changes so that the level of service can continue uninterrupted.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Patience with small things, patience with all things. Patience is not just a virtue it is a habit. While business seems to be moving faster than ever, it’s those small things like a first meeting, or getting that introduction. They take more time than we would like. It’s important to not push things so hard they eventually fall out of reach. This is the same with many things in life. When I was a kid, I had one speed, go. As I got older my speed switched to go faster. Patience became a sport to practice for me. It’s much easier to master a skill or habit on smaller things before you move onto bigger things and over time it just becomes natural.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
Honestly, I would focus on educating teenagers on how to become financially independent. We see a lot of this on social media these days, but most of it has no context or is designed as a marketing ploy. I think that if there were systems in place or an organization that made financial success truly available to kids through mentorship and curated events, it would have a natural trickle-down effect to the next generations. It would probably make a lot of parents happy too.
How can our readers further follow your work online?
You can find my LinkedIn profile here https://ca.linkedin.com/in/ct-falk or check out our website https://www.skrillo.co it is under a bit of reconstruction at the moment but we will be updating it more with access to newsletters and more resources.
Thank you so much for sharing these important insights. We wish you continued success and good health!
Appreciate it, the same for you!
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