Articles written by guest contributors

Weston Zimmerman

Increasing upsells through crew leaders
By Weston Zimmerman

Upsells are awesome! You are already on-site, have your equipment there, and your team is there as well. So, when upsells happen – BAM! Because all your mobilization costs are already covered under the original job, you increase your profit from that job. That’s just one reason.

Upsells have a lot of benefits and upsides:

  • Little to no mobilization costs
  • Instant cashflow (unlike normal jobs where you are scheduling it weeks or months out before you collect payment in full)
  • Higher profit margins
  • Easier to close (you are already there, gained the love and affection of your customer, easy peasy close)
  • Less admin work, scheduling, etc.

So, how can you get more of those awesome upsells? Empower and equip your crew leaders to be upselling MACHINES!

When I was in the field at Tussey Landscaping, my best year, I did over $300k in upsells at a $4 million (at the time) company. That’s more than 7% of the total company revenue! And nope, I wasn’t the sales guy. I was the foreman doing the work with the crew. And that was just me, 1 of 4 foremen.

The point I’m making is that you can make upsells a significant revenue/profit producer for your company. You just need an army out there making the upsells happen for you…. like your crew leaders.

Why your crew leaders?
Aren’t your crew leaders supposed to be just making the work happen? Of course, but every member of your team is there to make the company successful. If the company is successful, then everyone on the team can be successful too. So, I’m suggesting that as a crew leader, if you find opportunities to upsell, the company will make more money, then you can make more money.

Why am I focusing on the crew leader and not some other role? Well, because they are the ones spending the most time with the customer, building that relationship and rapport, keeping the client up to date on the job progress. AND, (this is a big “and”) clients tend to let their guard down and trust the crew leader’s opinion.

They don’t view it the same as when your salesperson shows up on their doorstep. They don’t expect to be sold to by the crew leader. So when you are getting close to wrapping up the job, and the crew leader suggests to the client, “Hey, we could add some path lighting to this new walkway for $——, and it’d be cheaper to do it now than if we’d have to come back. What do you think?”

Bam! Sold!

When I did this, the client often thanked me for the suggestion. They trusted my opinion.

Making it happen
So how can you make this happen? There are a few of things I feel are important to making this work out well for you.

  • Bottom line – everybody’s gotta win.
  • Define an upsell structure, make it easy. Be clear on how it works for each person in your company who does an upsell.
  • Provide commissions to the people that suggested and got the upsells.
  • Show/communicate to your crew leader any line items the customer didn’t go for on the original proposal as upsell suggestions.
  • Simple is better. Just make a one-pager with a few sentences that state something to the effect that ‘if you generate an upsell, you earn X commission,’ and define what an upsell is.
  • Promote the upsell program to your crew leaders.

It’s also a good idea to address how you handle splitting the commission if 2 or 3 people were involved in making the upsell happen. For example, if the upsell was complicated and required the help of you as the owner or salesperson, you need to be able to handle that. Or, if crewmembers and the crew leader tag-teamed closing the upsell with the customer, the crewmember needs to get a share.

If the upsell was simple and didn’t require the sales person to get involved (like selling lights at $300/ea or a pond kit that you had already pre-priced and the foreman was just selling it off your menu) then the crew leader/members could earn the entire commission.

Hint: here’s why having menu pricing for simple things is so powerful: Non-sales people can sell from it. At Tussey, we had menu pricing for all our water features. And we had flat “per fixture” pricing for lighting, making it super easy.

Commissions inspire employees
Make it enticing and motivating! At Tussey, we got 5% on water features and lighting upgrades, and 2% on everything else like hardscaping, landscaping, etc.

Make sure the cost of paying these commissions is figured into your pricing and into your budget. If you already figure out the commission of your salesperson into your pricing, then you’re good to go. The crew leader is just acting as another salesperson for you.

I’d also recommend a “Leader Board” in your shop or something where you show everyone’s upsells this year or quarter to inspire competition amongst your team to be the top upseller. Better yet, set a prize (paid day off, gift them a day on the lake with boat rental, gift card, etc.) for the top upseller of the year or quarter.

Line items in the original proposal that didn’t sell
This is a BIG one. I used this constantly! Every time I kicked off a new job, I’d open the SynkedUP app and check the Digital Job Folder for any line items in the job that were “On Hold.” These are items the sales person had suggested on the original proposal, the client rejected it, and now that particular line item was just sitting in the job, “On Hold.”

If your crew leaders aren’t doing this, show it to them in the app, and foster a culture of doing this. It is POWERFUL. It’s like a canned upsell opportunity.

I would also encourage your salesperson to always put optional upgrade items on the original proposal to the client, even if they believe the client will reject it or didn’t ask for it, just to plant the seed.

Then, if the client rejects it, that’s ok. It’s sitting there where the crew leader can see it and use it to suggest an upsell. The salesperson planted the seed. The crew leader comes in, wins the customer over, builds that rapport, and when the moment is right, suggests and often closes that upsell.

When I was at Tussey, the salesperson and I often communicated to do just that, and it worked like a charm.

What would it be like if you could boost your company’s revenue by 5%, 10%, or 20% without hiring another salesperson or driving to more consultations?

And, at the same time, your team would make more money, be more motivated, and you’d be providing a path for them to grow and think more like an owner. When employees feel that, I’m telling you, from personal experience, they stick around. They feel engaged. They feel autonomy.

Just make sure… keep it KISS. Keep It Simple Stupid.

And make absolutely sure… that when the company makes more money, and you make more money – that they make more money.

Follow through! Don’t say that in words and then not follow through. That’ll completely kill your credibility, the vibe and the energy you can gain from this.

What do you think? Gonna do it? Already doing it? Have any objections? If so, what are they? Let me know!

Weston Zimmerman is CEO & co-founder of SynkedUP project management software and app. SynkedUP helps contractors know and track their numbers, estimate and job-cost jobs, and manage their jobs efficiently. Email, call (814) 383-1901 or visit

Digital Edition
December/January 2024