Why CSMs should be your Secret Sales Weapons

When I first started at LeadUp, I was equipped with 6 months of cold calling experience, an idealist attitude, and a burning desire to impress my new bosses with my drive and curiosity.

I worked hard, closed a few deals, and ultimately realized that I thrive in customer success rather than sales (anyone else with a  “bleeding heart” will understand). So in order to utilize my strengths, we figured out a way to make customer success the bulk of my role.

Since transitioning from sales to customer success, I’m beginning to see some irony. It’s clear in my new role that customer success has helped my remaining ties to sales thrive. A few cold leads from last winter have since heated up (whoop whoop!), and I have been able to use my new perspective in approaching them.

But don’t worry – I’m not going to make you listen to the story of my resurrection as a sales rep. Instead, I want to share a couple reasons why CSMs might be your best bet for closing rockstar deals, or at least a few reasons they should be involved in order to accelerate the sales process:

CSMs can sniff out a good (or bad) deal a mile away

In customer success, we have the snout of a bloodhound when it comes to clients who have mismanaged expectations, bad tempers, or hard-to-sell products. This means that even if a prospect is ready to sign a check on the spot, your CSM will be the first to say “…let’s pump the brakes.” CSMs know they’ll be left feeling like this if they rush a deal:

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Equally as valuable, we can point out the deals that we should be fighting for. The ones that we know we can take under our wing and make our new golden goose.

The point is: CSMs seek the lifetime value of the deal above the initial payday, so you should seek their expertise when weighing whether it’s a good idea to push your hottest lead to sign on the line that is dotted.

The level of trust and loyalty skyrockets

As I started talking to potential clients while in my customer success role, I realized that I was using anecdotes from my best clients in my pitch to them. This tactic was instantly more attractive than a standard value prop because the potential client could mentally plug themselves into the story – with me still at the steering wheel. Their trust in me was already miles ahead of where it would normally be because they knew I was talking to them as their advocate and their partner.

Knowing that I’ll be with them through every part of their customer journey motivates me to take extra consideration to manage expectations and give advice on the most beneficial timelines to meet their goals. A successful client relationship starts with a very clear  explanation of what on-boarding, ramp up, and the contract execution will look like. Our comfort in communicating contributes to a feeling of loyalty, and ideally, this will translate to a longer and happier relationship between the CSM and client.


I hope for all you CSMs out there, this inspires you to take a proactive approach to becoming involved in your company’s sales process. For the account execs and sales reps still reading, I have the utmost respect for your process and hope these thoughts help you guys close the best accounts possible. Look out for more thoughts on Customer Success and Sales collaboration coming soon!


Why Being Comfortable Should Make You Uncomfortable

If I’ve learned one thing this year, it’s that comfort and satisfaction aren’t what we should be striving for. Especially in a start up, the worst thing you can do is come to the office and do the same thing every day with no motivation to question your organization’s process.

I want to give a shout out to Change today. Change can be frustrating, difficult, and uncomfortable, but despite that, it’s vital to success.

Why? Because it makes us better. A lot better.

I’m not talking about the kind of Change where you grapple over logo colors or the right adjective to include  in your value prop–I mean the really uncomfortable, the “I’m going to scream because I wish I could just do it the old, easy way,” kind of change.

Our team has been through some big, roller coaster, hang-onto-your-hat twists and turns over the past 15 months. But you know what came out of everything single one of them? Improvement. Organization. Clarity.

Here are a few things to tell your brain to look out for to make positive changes in your process:


The day where I don’t learn something from one of my clients or my team is the day that I should be fired (Mark and Patrick, if you’re reading this…just kidding).

Your clients and your coworkers are the easiest sources to draw inspiration from because they are overflowing with positive and negative feedback. Don’t shy away from their comments or treat listening to their criticisms like a chore. Even the simplest feedback can hold valuable lessons for future process improvements.

Failing aggressively:

To be truly successful is to have known failure and learned from it.

I’m lucky to have bosses that not only allow me, but encourage me, to fail. Sounds weird, right?

But stay with me. Every time I come to them with a slightly weird or off-beat idea, I have permission to try it as long as I think it will make my day-to-day more beneficial to my clients or make me more efficient with my time.

I know what you’re thinking: “What if you’re wrong and you burn down the office?!”  

My response to you is: “Who let me near fire in the first place?! That’s a terrible idea!”

But seriously, if you fail, you just go back to the old way of doing things. But if you don’t fail? Then you created a better process for your whole team, you improved your client retention, and you’re a hero for the day.

Constructive conflict:

This one’s the most uncomfortable, but potentially the most valuable.

Think back to your freshman year of college. Once you stop cringing at the your poor fashion choices, I want you to think about your first group project. It was pretty rough, right?

Why? Because each person had their own way of communicating, writing, studying, and presenting. What a MESS. Well, guess what…. Those people followed you to adulthood. They’re called your co-workers.

Thankfully, we’re a bit more well-behaved and mature than we were in college, but the differences in perspective and thought process remain. That’s where opportunity comes in.

I can tell you that I have been on a different page (maybe even in a different book) with thoughts and ideas for our team, but once we all share our thoughts fully and take the time to listen to each other, we are able to take the best parts from all of our brains and smash them together to make a beautiful, powerful solution.

Sometimes those conversations go smoothly, and sometimes they take a few bumps to get there, but we always end with something greater than we could have created on our own.

My Challenge to you:

Change something about your day today. And tomorrow. And the next day. Start with something small and then move to something a little scary, difficult, or challenging. Share it with a colleague to keep you accountable on the outcome. And challenge them to Change, too!

It may be uncomfortable at first, but once you start to see yourself making positive impact, you’ll never settle for comfortable again.



How I Turned an Icy Cold No into a Sizzling Yes

As a Customer Success Manager (or Inbox Ninja as we call it around here), the majority of my day focuses on taking a soft objection and transforming it into a warm lead for our clients. The other part of my day revolves around drinking coffee and catching Pokemon that sneak into our office – but that’s beside the point.

It’s become obvious to me that while choosing the right people to reach out to is important, identifying who has authority is the game-changer.

Let me give you an example.

One of my favorite clients creates customized experiences to help companies build more cohesive teams and better leaders (seriously cool stuff – ask me about it later if you’re interested). A few weeks ago, a Organizational Development Manager responded to one of my outreach emails on their behalf with a very stern “no” – it seems they were in a hectic transition phase and he did not have time for this right now.

What I wanted to say was…


But don’t worry. I kept my cool and assured him that I would reach out in a few months when they were through the transition.

Not even an hour later, an employee from the same company sent me an excited response that she’d love to chat with our company. Apparently, this is just what they needed! Woohoo!!

And guess who it was? The first respondent’s BOSS!

Boom. Roasted.

Long story short: my client had the meeting, closed the deal, and we all lived happily ever after. We weren’t discouraged by a no that really could’ve meant “I’m in the middle of something” or “I haven’t had my coffee” (which are both totally reasonable).

Three Takeaways:   

  1. Reach out to more than one contact: One person seldom has all the say in a decision to bring on a new vendor. Share information with people on different teams that would be impacted by the service you provide. Make sure you cover various departments that make sense and a variety of levels of employees.

  2. Don’t give up: The first response will probably be a “no”. That’s just life, ya know? But that doesn’t mean one of the other several people you reached out to won’t see exactly what they need in your outreach. Trust the process.

  3. Always be respectful: Please don’t use this post as permission to spam every employee at your dream company with the same email. Targeting is key. It’s also vital to acknowledge and comply with a “Please take our team off your outreach.” We’re not trying to make any enemies here – only give the right people a chance to say yes.

I hope this gives all you hard-working sales warriors some inspiration today. I’m rooting for you!

Keep Calm and Ninja On,