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How I Lead: Jack Delosa, The Entourage

Jack Delosa had seen a gap in education and training for business owners, which was holding them back. To solve this – helping them grow their businesses and become better leaders – he had a clear idea of the type of business he wanted to run and the leader he wanted to be.

Delosa has built process, systems and teams to enable growth of The Entourage, support the SMB leaders who are its members, and allow him to become the CEO he intended to be. 

Here, he shares his story.

I created The Entourage because I was dissatisfied and inspired in equal measure. I’d seen just how little traditional education does to prepare people for the real world of business and was frustrated by a lack of proper education for business owners. 

Having long believed in the nobility of entrepreneurship and the ability of entrepreneurs to foster innovation, I was disappointed by the lack of resources available to those wanting to take that path. 

So the inspiration and ambition to build The Entourage were there in abundance. But so were the challenges. 

From spreadsheets to CRM

In the early years we had an operational messiness to us because we didn’t have the right CRM in place. Being a membership organisation, this posed challenges that we needed to address swiftly to ensure our members had great customer experience (CX). 

Despite the fact that our members are everything to us, we were managing our entire membership on a spreadsheet that didn’t get updated properly, there was very little continuity in the journey from marketing to sales and beyond, service was frustrating. Basically, CX was suffering and our attrition rate was high. 

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Employee experience wasn’t much better – new staff coming on board were overwhelmed by the complexity and enormity of what they had to get a handle on. We were fighting to keep our heads above a flood of administrative mess. 

None of this was funny at the time of course. But with hindsight it’s hard not to laugh at just how cumbersome we made our own work.

“Do what you say you’re going to do”

We always cared for our members but now they know we care for them.

Deploying the right technology helped hugely. Integrating our customer data with a CRM system, having access to real time updates, building a 360-degree view of the customer — all this meant we could offer vastly improved CX at every point of a member’s journey with us, delivering a continuity and consistency we previously had not. 

Interestingly, when the technology gave us the means to track and analyse the nature of customer complaints, we found they were overwhelmingly about things that may have seemed small on our side of the relationship, but cause exasperation on the member’s: not returning a call when we said we would or not replying to an email query. 

Having the right technology means we can really build trust into member relationships by not dropping the ball on the ‘little’ things that escalate into big frustrations. 

I believe that delivering on the basics is at the core of trust. Simply put, do what you say you’re going to do, deliver what you say you’re going to deliver. Big gestures and fancy flourishes are all very well. But the surprise and delight aspect can’t get off the ground until you’ve got that fundamental reliability in place.

Using innovative technological solutions also impacted the employee experience, allowing the team to do the high-value, satisfying work of nurturing member relationships and helping members to achieve their goals, instead of chasing their own tails and constantly apologising.

Beyond buzzwords: Vision and values

With those changes came the space for me to develop my leadership style and approach – to become the CEO I’d intended to be instead of consistently trying to put out fires. 

There are two components I believe are essential to successful leadership.

The first is having a clear vision for the organisation and finding people who are aligned with that vision. In our case, that means finding people who value education. Perhaps their parent was a teacher. Perhaps they didn’t finish school or they didn’t enjoy university and want to see change in education. 

The seed of an idea can link to our vision, but it has to be there in some form. People love to be part of something that’s going somewhere and a vision can provide that drive. Indeed, it can often be more compelling than a raise. 

The second crucial component to successful leadership is the clear understanding and articulation of an organisation’s values. And by values I don’t mean grab words like ‘honesty’ and ‘integrity’. I mean the unique principles that govern and guide who you are, how you behave, and how you communicate as an organisation. 

Values require time, reflection and commitment. When properly developed and realised,  they enable stakeholders to care about and believe in the business beyond the financial gain. 

Making time to make change

One of the things I’ve really enjoyed being able to dive into as CEO since we’ve been made these operational changes is a process we call ‘empathy mapping’. This allows us to develop automated sequences that speak authentically to the emotions of a member at any given time in their journey with us. 

For example, in week one of membership, we know they are excited. In week four, they usually feel a bit overwhelmed. In their first quarter with us, they consume a lot of training so at the three-month mark they’re feeling significant pressure to implement what they’ve learnt. 

Six months in, they’re enjoying the benefits of the community. And by month nine, they’re wondering what comes next. Empathy mapping has meant we can be there for them, understand what they are thinking and feeling, and respond with the right resources at the right time. 

Innovation helps move the world forward and our vision is to enable and empower entrepreneurs to do exactly that. Transforming the operational abilities of The Entourage has empowered me as a leader to anticipate and meet the challenges ahead, and stay true to the course of that vision.

To find out more about the motivations, challenges and solutions of SMB owners and leaders, as well as the trends that will matter over the coming 12 months, download the Salesforce Small and Medium Business Trends report.

Small and Medium Business Trends report

Salesforce Staff

The 360 Blog from Salesforce teaches readers how to improve work outcomes and professional relationships. Our content explores the mindset shifts, organizational hurdles, and people behind business evolution. We also cover the tactics, ethics, products, and thought leadership that make growth a meaningful and positive experience.

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