Travel Tips for CSMs

Airplane Wing Branded.png

By Kristen Hayer

I’ve been on the road about 50% of the time this year, and my life has been a blur of airports, hotels, Lyfts and conference rooms. There have been days when I woke up in a chain hotel and was confused about the city I was in because they all look the same (still love you, Marriott!) After several years of being heads down building our business, this year has been like a travel boot camp for me.

I know many of you are CSMs and CS leaders who also travel. It can be grueling, especially when you have other customers and email to tackle when the day is done. I thought it would be fun to share what I’ve learned about optimizing travel time, and to hear your travel tips as well. Here’s my list, in no particular order:

Get a Work Space Membership

It can be a little depressing to spend the day working from your hotel room, and the wifi in coffee shops can be sketchy. If you often find yourself in big cities, it is worth $50/month for a WeWork (or similar) membership so that you have a professional workplace with perks like fancy water, phone booths, and fast Internet. Alternately, ask your client if they would be willing to let you take over a conference room for the day.

Stick to an Airline and Hotel Chain

Of course, points are great, but the side benefits to membership programs are sometimes worth more than the points. If you’ve been following our blog for a while you know I am a Delta fan. If you’ve ever met me in person you also know that I’m almost 6 feet tall. As a Gold Medallion member on Delta, I’m almost always upgraded to free Comfort Plus seats, which have 2 extra inches of legroom. That is everything to a tall person!

Work Between Meetings

Working a full day with a client and then having hours of work to do at the end of the day to catch up is rough. I find that even if I’m onsite with a client for a full day, there are breakpoints throughout. If I have to choose between working during the breaks or working into the wee hours of the night, I’m going to choose the breaks. If you make the most of that time you can really cut down on evening work, which frees you up to…

Work Out

This is the hardest thing for me to do when I’m traveling, so I’m definitely not coming at this from a place of perfection. However, when I take my workout gear I’m more likely to work out. When I schedule my workouts I’m more likely to work out. When I choose a hotel with a gym I’m more likely to work out. If I work out, I’ve noticed that my travel is smoother, my mood is better, and any time zone changes have less of an impact.

Keep a Go Bag

This sounds a little like the beginning of a zombie movie, but it is just a small bag with travel size toiletries plus a complete 2nd set of makeup. I store it in my suitcase, and it keeps me from forgetting stuff and having to buy things on the road. If I’m totally honest, my go bag is largely made up of stuff I had to buy on the road because I forgot things. Now I don’t have to worry about it. Pro Tip: If you like moisturized skin, sheet masks are easy to pack and make for a relaxing end of each day.

Drink Water

I used to travel on a combination of coffee, diet soda, and a glass of wine to wind down. That is a recipe for dehydration, bloat and poor sleep. After reading a number of articles written by flight attendants, I switched to water when I travel and cut (most of) the caffeine. I’ll still have a glass of wine, but I make sure I’m hydrated and drink a bunch of water afterward. It may seem counterintuitive, but less caffeine and more water makes you more alert.

Find the Fun

My favorite business trip, hands down, was a trip last summer to Memphis. I was out there for a client kick-off meeting, and got in the day before. I ended up with a morning to kill before things got started, and decided to visit Graceland. It was fun to see something uniquely Memphis, gave me something to talk about for the entire visit, and made the trip a nice balance between work and business. Think about how you can weave a little fun into every trip.

These are my travel tips, but I’d love to hear yours. What do you do to make travel amazing? How do you get all of your work done on the road? How do you find a solid work-life balance? Please share!

Need more practical Customer Success tips? The Success League is a customer success consulting firm that offers a CSM Certification Program that starts this week. For more information on these classes our workshops, and consulting services please visit

Kristen Gray Bio.png

Kristen Hayer - Kristen believes that customer success is the key to driving revenue, client retention and exceptional customer experiences. Her areas of expertise include developing success goals and metrics, designing the optimal customer journey, selecting technology, training teams, and building playbooks. Prior to founding The Success League, Kristen built and led several award-winning customer success teams. Over the past 20 years she has been a success, sales, and marketing executive, primarily working with growth-stage tech companies. Kristen has her BA from Seattle Pacific University and her MBA from the University of Washington.

Last Chance to Sign up for our CSM Certification Program TODAY!

Stopwatch Branded.png

You still have time to sign up for the Spring/Summer session of our new Certified CSM Program and start tomorrow, Thursday, May 23rd. This 16-class series will build your skills in all facets of a customer success role including developing account plans, managing a portfolio, onboarding new clients, conducting business reviews, managing a sales cycle, leading cross-functional teams, and tackling difficult conversations. Please see list of classes below.

Uncovering Opportunities
Asking Great Questions
Objections & Negotiation
Managing a Selling Cycle
Using CRM and CS Systems
Cross-Functional Leadership
Difficult Conversations
Career Development for CSMs
Customer Goals & Outcomes
Business Strategy for CSMs
Managing Your Portfolio
Kicking Off The Relationship
Executive Business Reviews
Renewals & Churn
Customer Advocacy
Time Management for CSMs

Looking forward to seeing you in class!

Strikedeck Radio - Episode 54


In Episode 54 of our Strikedeck radio podcast, Kristen is joined by Andreas Knoefel to discuss the Customer Success Performance Index. Andreas is a highly experienced CS leader, a CS Management Consultant, and a partner in developing the CSPI. This unique tool is available to the public and allows CS leaders to benchmark their company's performance across 8 dimensions of best-in-class customer success. Tune in now!

Strikedeck Radio is a partnership between Strikedeck and The Success League. You can subscribe on Apple PodcastsGoogle Play, and anywhere else you get your podcasts or follow us on LinkedIn or Twitter to get updates on new episodes.

Product and CS: The Intersection Begins

Two Paths Branded.png

By Lauren Costella

Do you know what gets me jazzed (yes, I said it, jazzed)? Seeing the continued overlap of Product and Customer Success teams! This is a monumental time in Customer Success because software companies are popping up everywhere to help us better understand who our customers are, what they are doing within our software (or how they are using our products and services - non-SaaS based), where they get stuck, and more importantly, where they derive value! Here are just a few that I’ve come across as a CS leader: Amplitude, Pendo, Mixpanel, and Piwik.

As CS Leaders, if we aren’t driving value for our customers, we aren’t doing something right. The difficulty comes with understanding what is actually valuable for our customers, especially given a diverse portfolio of needs. And if you’re like me, you know that sometimes what customers say and what they do are totally different things. What signals are you using to understand customers and whether they are getting value? At the end of the funnel, you might be looking at retention and growth, but you need earlier driven signals that differ by different cohorts of need the same insights that product and engineering teams have, and that’s usage data!

This has been topic of discussion in the CS space for some time; however, it’s one that isn’t the simplest to start. It’s critical, then, we not only keep that conversation going, but that we also keep pushing each other toward getting more analytically, data-driven insights into our health scores. We need to trigger actions and playbooks (risk and growth) based on that data, and we need to strive to be truly “proactive” by getting to a point of “predicting” value achieved (or not), instead of reacting to it.

In the spirit of helping you to start simple, let me offer a few tips to get you going in the right direction. And if you're looking for more insights, check out more blogs on The Success League or check out another group of which I’m a part, the Customer Success Leadership Network (CSLN) meet up from January of this year.  That meet up had both CS and Product leaders providing their unique perspectives on how best to work with each other.

3 Tips to Help You Get Started with Product & Engineering

1) Make Friends

When was the last time you met with your head of Product? If it wasn’t in the past week, think again. If you’re going to start building the foundation of insights, start by talking about issues on a regular basis. Set a cadence and stick to it. As an executive leader for Medrio, I meet with each of my co-executives once per week to discuss issues uniquely between our departments. It’s revealed gaps and insights and creates better alignment as we develop customer strategies that require resources on both sides.

For example, when I first started meeting with our CPO, we began with support ticket data. I could easily show our CPO that product releases were killing the team. Why? Bugs and/or “expected” functionality that presented like a bug or let’s face it, missing essential functionality all together. By starting with some simple data, we were able to identify gaps in process and systems for improvement.

2) Co-invest in User-Friendly Systems

Which leads me to my next point: co-invest with Product teams in software/systems, which are user friendly and give you insights into what your customers are doing, why they are doing it, when they are ready for more product/services, and where they get stuck. Your Product teams are (or should be) looking at these types of insights all of the time. The issues I’ve seen is that the information is typically siloed and difficult to decipher.

For example, our Product teams uses Splunk to track a lot of our customer analytics. To use Splunk, however, you need to understand SQL and programming language to produce any meaningful insights for customers. In other words, our CSMs or CSRs (and sometimes our Product Managers), can’t simply go in and get a list of all studies with more than our best practices for variable counts on a page or skip logic used in a study. Forget about it, you need a engineering degree to pull that data! Which means, we (as a CS team) are constantly bugging our Product and Engineering teams to create those insights for us with dashboards and reports. What a drag for both teams!

Which is why I say: co-invest. Put up some of your CS budget to get the insights you want in a user friendly way, and it’s likely you and your Product and Engineering teams will be thrilled to get you what you need without having to do the heavy lifting.

And let’s face it, with a user friendly system, both teams don’t have to guess what they think is the greatest value to a customer; rather, we would be able to just see it (and see it by different cohorts). And armed with that information, our product teams can either create better product based workflows or we (in CS) can create better best practices to achieve winning customer strategies.

3) Share Joint Success Metrics

Finally, I recommend sharing joint metrics with your Product teams. Our Chief Product Officer is held to joint metrics with my team including Net Retention (Upsell + Retention) and Customer Satisfaction. At the same time, my team is held to metrics that help his team drive efficiency and results. My team keeps mis-classified bug tickets below 10%. At one point this was 30% and by reducing that to under 10% and keeping it there, we’ve reduced costs in Product and Engineering by $160K per year. That’s significant savings in costs and time that could be used elsewhere. Additionally, my team is held to helping with product adoption: a metric the product and engineering team follow after every release. We educate customers, help them use the product, and ensure they are well trained. Joint metrics keep us both incentivized to ensure great communication and working together, which only produces better results for our customers.

If CS is the map to driving value for Customers, then Product (and associated analytics) is the key for deciphering it. We must work together to manage how to understand leading risk factors and more importantly, reasons and paths for retention and growth! What path makes our customers stick? If you can’t answer that question, it’s time to start building toward answering it. Let’s commit to that quest. As the VP of CS for Medrio, and I’m committed to driving success of customers with Product and data driven insights. Can I get your commitment too? Let’s do this!

Need help figuring out how your Customer Success team can better collaborate with Product and Engineering within your organization? The Success League is a customer success consulting firm that offers a Leadership Training Program as well as Leadership Coaching. For more information on these programs and other classes and engagements please visit our website at

Lauren Bio Final.png

Lauren Costella - Lauren is a change agent, communicator, leader and passionate champion for Customer Success. When she’s not working as the VP of Customer Success for Medrio, you can find her serving as an advisor for The Success League, a board member for the Customer Success Network, and blogging on the CS Playlist. Lauren has her MA and BA from Stanford University. She was a former USA National swim team member and enjoys staying active in the Bay Area.

Key Topics in CS Training Series Begins Next Week!

Keystone Branded.png

Do you need a thorough overview of Customer Success best practices? We have a training series for you! This introductory, 8-class series is designed to build the skills you need to tackle core customer touch points like setting goals with customers, onboarding new clients, holding effective business reviews, and managing renewals. This round of classes is offered at a new time: 12pm Pacific / 3pm Eastern.

5/23 - Customer Goals & Outcomes

5/30 - Business Strategy for CSMs

6/6 - Managing Your Portfolio

6/13 - Kicking off the Relationship

6/20 - Executive Business Reviews

6/27 - Renewals & Churn

7/11 - Customer Advocacy

7/18 - Time Management for CSMs