How I successfully hired, trained, and handed off the sales role at Lead Cookie
One of the things fellow entrepreneurs ask me about the most is how I managed to get out of the sales seat at Lead Cookie. For many entrepreneurs, this is one of the hardest and scariest things to let go of since it is so closely tied to revenue.
Yet, your fears are grounded in reality. The first time I tried this, I failed. The second time, I succeeded.
In this post, I will walk you through the process I went through to hand over sales.
Where I am at today
Today, Lead Cookie sells 100% without me. Occasionally, I may support in closing a deal with someone who is a long time personal contact, or for something that is a large partnership including many accounts.
But other than that, the talented Isaac Marsh handles everything.
With that being said, I do want to clarify one thing. Handing off sales is not the same as handing off marketing.
While Isaac can 100% close deals and had them off to the team without me, he is not also acting as the head of marketing. Without leads, Isaac would have nothing to close.
Unfortunately, I learned this the hard way by stepping back a bit too much after handing off sales. Instead of doubling down on marketing, I let the marketing momentum that we had carry us for quite a while until the lead flow started to slow down at one point.
It was only then that I realized, "Oh crap, marketing is still on my plate." While we do have some marketing systems in place, it's clear that this responsibility still sits in my lap.
So be sure to not think of "Sales and Marketing" as one in the same with handing them off.
Sales is closing deals.
Marketing is generating them.
How I failed the first time I handed off sales
The first time I tried to hand off sales, it was a disaster that ended with me having to lay off 6 team members...
The consequences of screwing this up are very real.
There are a number of mistakes I made the first time I handed off sales.
Too early - I tried to hand off sales at roughly 10 months into the life of the business. We were too young and still had so much to learn and dial in on our sales process.
Too ambiguous - This is probably the biggest mistake I made. The sales process was far too ambiguous and in my head. I had tried to document some things but ultimately, when I tried to hand it over, it was far too vague.
Too fast - The next mistake was that I tried to hand off sales way too fast. In the span of about 1.5 months, I attempted to offload it completely and hand the reigns over to someone else.
Too inefficient of a sales system - Once I failed and took it back over, I realized how much of a massive improvement there still was on our sales systems. So we automated nearly everything in our CRM, our deal closing process, our invoicing, our follow-ups, etc. The entire post I wrote about the Lead Cookie Sales Playbook: Automating the Close... that all happened after I failed.
Tried to hand off too much at once- I tried to hand over everything at once. Account management, sales calls, and handling inbound leads. I tried to drop the entire workload of sales on someone else's lap all in one fell swoop, as opposed to gradually having them take piece by piece.
I overwhelmed my salesperson - All of the points above led to an overwhelmed person running sales who failed at the role. Yet, the failure was not their fault. It was my own for all of the points I previously mentioned.
How to succeed in handing off sales
After failing at handing off sales the first time, I was pretty scarred. Six layoffs are something no one ever wants to have to do again. So I held onto the sales seat for the next full year of the business.
Step 1) Build and refine your sales process
During this time, I refined the hell out of our sales process. I automated everything that I could. I created better marketing materials. I trained VAs to help me with small daily tasks.
Eventually, I documented everything into our Lead Cookie Sales Playbook. You can see pieces of that through the articles below.
The Lead Cookie Sales Playbook
All of this refinement happened as a result of my first failure. I knew that if I wanted to hand off sales successfully, I needed to figure it out myself. I wrote about this in more detail in my article on the mistake to avoid when hiring a salesperson.
As you are refining your sales process, here is your goal.
Before you hand off sales, you want it to become robotic. You want it to be a system and a process that someone else is simply taking over.
This is a key point here. The big mistake that i made before, and what I see most entrepreneurs make, is saying, "I have a sales problem, so I am going to hire a salesperson."
Or they don't know how to build a sales process, so they think they can hire someone to build it for them...
Here is the deal. I work with Damian Thompson as a sales coach and even he will tell you that you can't just hire anyone to come in and build your sales process. Any salesperson capable of that is going to be either extremely expensive, or working somewhere making a ton of money.
Instead, you must build your sales process yourself and then hire someone else to operate it.
So don't make this mistake.
Build your sales process first, then proceed to the next step.
Step 2) Find someone to fill the role
Once you have your sales process defined, you need to find someone to fill the role and start closing. Damian recommends hiring two people to take over the sales role with the assumption that one will probably fail.
Yet, in reality for me, that wasn't the case. Here is how I ended up filling the role.
Through my network, I knew two guys who were running a small cold email and outbound consultancy. They were doing well and were amazing at the work they did, but they weren't loving the entrepreneurial side of it. They were amazing at their craft, but were overwhelmed in the "running the business" part of things.
I approached them about coming on board and they were very receptive to this. They ended up coming on board as our salesperson and our second strategist for Lead Cookie, which helped create more redundancy and stability for our team.
This was a huge win and a game-changer for the company. But let me stop to point out a key lesson here for most service companies looking to replace yourself in sales.
Consider hiring a freelancer or consultant as a salesperson.
For most service-based companies, your sale is not transactional. You're not selling a product, but instead a service. As a result, there is almost certainly a consultative aspect of your sales process.
At Lead Cookie, Isaac isn't just closing any lead who comes in the door. He is the "gatekeeper" and has to filter out leads who are a bad fit from the ones who are a good fit. He has the ability to do that because he has years of running outbound campaigns.
And here is the thing... there are certainly freelancers or solo consultants out there who would love to join your team. They are great at their craft and they love the work they do. But they HATE running their own business.
You would be amazed how prevalent this is. At Content Allies, I have followed this same framework to hire my lead strategist and head of podcast production.
So instead of just posting on job boards to find applicants for this role, consider going out in your network and seeking freelancers or consultants who operate in your world of expertise.
Have your salesperson work in an ops role for a short period
This is one other nugget that helped in this process. We had Isaac work in all of the other roles of the company for about a 1-2 month period while he was training for sales.
This helped us monetize him in the short-term while training, and it was invaluable for him to see how the entire business and systems work. He did everything from account strategy to the simplest VA tasks.
I can't stress the value of this enough.
Step 3) Train and transition
The next step is the training and transition. Before you enter this stage, you should have a documented sales playbook and a refined process as much as you can.
At this point, it's time to start training and handing off the roles. Here is what I set out for with my training goals.
Goal: In 90 days, Isaac is able to handle closing deals from inbound to operations all on his own.
Phase 1: Training and Shadowing: Isaac to meet with Jake for sales training and shadow sales calls.
Phase 2: Isaac to handle sales calls with Jake shadowing.
Phase 3: Isaac to handle sales calls without Jake shadowing.
Those were the high-level goals and milestones we aimed for. And at the end of the 90 days, I had a week-long vacation planned so we had to make it happen.
Within those high-level phases, there were a few other things we transitioned over.
Inbound lead management - At first I cc'ed Isaac on email communication with all leads so he could see how I communicated with leads, how I booked calls, etc.
This was one of the first things we handed over. He started scheduling the calls even when I was running them. I was able to stay cc'ed on all email threads and provide feedback at any point.
CRM management and follow-ups- Once Isaac took over inbound lead management, it made sense for him to start handling the CRM and follow-ups. Even when I was running sales calls, he would send out the emails after the call and follow up with the lead.
Entering closed deals into our systems - After I would close a deal, I would have Isaac enter the deal into our system and hand the new opportunity over to our operations team.
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All of those small pieces of the puzzle were handed off, even while Isaac was in Phase 1. This made the transition nice and slow and let him tackle 1-2 new things each week.
Transitioning to someone else closing
Eventually, once Isaac felt ready, we started having him close deals on his own. I still shadowed and joined on all of the calls. This was important because in the early days there was a lot of "defer to Jake" when he got a difficult question that he wasn't ready to answer.
This also enabled me to coach and provide feedback on each call on what he was doing well and what could be improved.
Step 4) One-on-ones for ongoing alignment
Once you make it through the phase of actually handing off sales, the job doesn't end there. You still need to hold regular one-on-ones with your salesperson for ongoing alignment.
There will be ongoing questions or new challenges that pop up on a weekly basis. And considering that this person is on your front lines to new revenue, you want an open line of communication with them so you can catch any issues or concerns early.
When lead volume drops, Isaac is the first one to see it.
When sales are good and we are getting busy, Isaac is the first one to see it.
Be sure to keep weekly one-on-ones for ongoing coaching and to keep a pulse in your business.
Watch your numbers
One final element is to make sure to watch your numbers in this time period. You need data so you can know if the salesperson is the problem, or if something else is. Here is what we track on a weekly basis.
MQL's - How many new leads did we get this week?
Sales Calls - How many sales calls were held this week?
Closed deals - How many deals closed this week?
This helps us see problems early. When MQL's drop, we know that the other two metrics will soon follow.
Know your numbers and keep an eye on them as it's a very new experience once you are no longer on the front lines closing deals.
Handing off sales is hard work, but it's worth it
It took a lot of time and energy to get to the point of handing off sales. And while it was in transition, it was even more work than usual. Trying to run sales while training someone new was painstaking for that first period.
But once you make it through on the other side, it's amazing for two main reasons.
Freedom - Previously, I could never take extensive time off from the business because the business could not sell without me. Anytime I went on vacation, all I could think was "Gosh, there are probably great leads in my inbox. I'm losing sales every day I don't respond."
When I took that first vacation for a week, I hardly checked email. And we had closed 3 new deals while I was gone. That was an amazing feeling.
Growth - The other amazing thing is that we had reached a bottleneck in our growth with me in the sales seat. With everything else I was doing in the business, I was literally bottlenecking sales because I didn't have enough time in my calendar to handle sales calls. Oftentimes, leads had to book out 1-2 weeks in advance to get on my calendar... and that was killing our conversion rates.
On top of that, I literally wasn't following up with anyone. I was so overwhelmed that I was not even sending follow-up emails because I just didn't have the time.
Putting someone new in this sales seat was amazing because it let them focus on doing this job well, including all of the parts that I didn't have time for.
This helped us break through our glass ceiling and hit new levels of growth.
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So there you go, that's the high-level process of how I handed off sales at Lead Cookie. If you are going through this process yourself and need some help, feel free to book a Pick-my-brain session. I've talked numerous other entrepreneurs through this same transition and I'm happy to help.