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How to drive alignment between Sales and Customer Success

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matt (RevOps Co-op): Today we're going to chat with Christine Whitehead, VP of Operations at Replayz, about all things sales and customer success, and how to drive alignment between pre-sales and post-sales. Christine why don't you do a quick introduction for us, tell us more about you, your background, Replayz, and why this topic of sales and customer success alignment is so meaningful for you?


Happy to matt (RevOps Co-op) I’ve spent over 25 years in Sales, Leadership and Customer Success roles within the B2B, B2C and CPG spaces and am now working for my 5th start-up, just launched my Operations Consultancy business and am also in product development for another business.

Having spent the better part of my career in sales and CS, I believe I have a perspective that those who have only spent time on one side of the table or the other just does not have.

Many companies don’t have an understanding of the importance of bridging these 2 sides, and I hope this conversation today helps people see the importance of working together.

matt (RevOps Co-op)

I agree completely - I feel like we so often we think about marketing and sales because it's what drives new business and new logos, everyone likes those shiny new things but what we forget is that our existing customer base is where we actually generate our revenue and they can sometimes be a great source of NEW revenue as well and it seems that CS is typically forgotten about or not discussed at all within the realm of RevOps, so much focus top of funnel.

Trevor Greyson (RevOps Co-Op)

Everyone loves logo points but real ARR is in the Renewals!


“but renewals are so much easier… i mean they are already a customer!” -every AE


I agree completely. Some of the best growth I’ve seen for a company in my book of business has been growth within existing customers.

matt (RevOps Co-op): let’s start with the why - any opinions on why the sales to CS handoff can often be forgotten?


Sales teams are very focused on closing the business so they can move on to the next deal. Once handed off, they are no longer “responsible” for what happens. They’ve done their part.

Which could not be further from the truth.

Customer Experience needs to be a team effort.

When Sales and CS work closely together the customer sees the alignment and knows that they will be in good hands throughout the lifecycle of their journey

matt (RevOps Co-op)

Sounds like you've probably got a few horror stories to share 😈 😉


We only have an hour.  LOL

matt (RevOps Co-op): Actually on that topic, can you provide one or two examples/stories of things you have seen here that have gone POORLY and then a counter point on things that have actually gone WELL?



I remember one company where we had a 3 year mid six figure account that the rep had been working for nearly 2 years, they finally discounted the heck out of the service and made dozens of promises about the functionality of the system but had no idea that we could not do 1/3 of what they promised.  Once they were handed off, the customer became increasingly irate through implementation demanding that our developers spend hours getting the system to do EXACTLY what the sales rep promised.


When we explained that we were not at that point in development to do all the things they were asking they demanded to be let out of their agreement.

So the company did not lose more money by scrapping all that was on our current development roadmap, we kindly let the customer out of their agreement.

It was a tough lesson for this rep to learn and it tarnished the company reputation.

matt (RevOps Co-op): In that example, what are some things that could be implemented to improve the situation? Is it the need for a sales engineer to be included in the sales process? Tighter call review process by sales management? Looping in CSM / IM to pre-sales conversations?


Had the rep spent time talking to the CS team (who was in charge of implementation) and the development team, they would have learned more of the actual functionality of the system and what was on the development roadmap so they set the customer up for success.

Keegan Otter (RevOps Co-op)

I give so much credit to my early days of success and quota crushing at Outreach from pairing up with the CSMs who knew what the customers really loved about the product (and didn't like).


The rep had their eyes on the end game and not what happened after the pass off.

Shortly after that situation, CS and Development began meeting weekly with the reps to share this type of information so the reps were more “in the know”

We then implemented a “week in the life” scenarios between Sales and CS. It allowed us to bridge the gaps in processes so this type of situation was mitigated.

matt (RevOps Co-op): on the topic of weekly syncs, any cross functional cadence that you've seen work well? In my last role, we had functional meetings every week (e.g. sales, marketing, CS, etc.) but then relied on the departments to stay aligned with each other throughout the week and am wondering if it'd be better to have a general "GTM get together" every week to do detailed reviews of each department and GTM as a whole?


Allowing new reps to observe the cross functional teams as a part of their onboarding process, so they see a greater picture and understand where they fit into the puzzle has been quite successful.

This allows them to ask questions of the different teams and can better articulate the fit and function to the customer

Keegan Otter (RevOps Co-op)

The more questions you ask in the beginning from various departments the easier it all comes together which helps you as the seller become the real product expert and know when it is a fit or not. Preach this! This is what more orgs need to be doing

matt (RevOps Co-op)

that's a good takeaway Christine - make sure to include Customer Success, sitting through an implementation or participating in a QBR, as part of the onboarding process for new sales hires

Keegan Otter (RevOps Co-op)

This ^ is how sales reps are successful- Great advice Christine


In another situation, we had a client who was waiting on another vendor to implement their product before being fully ready to implement our service, but they were eager to sign their 3 year agreement so they would be able to execute immediately upon successful implementation.

3 weeks after they signed with us, the customer called me and said “I don’t know how to start this conversation, but I am going to have to cancel our contract before we even implement”

I was patient and asked them why and they explained that the other service they had been implementing was taking much longer than anticipated (was supposed to be a 90 day implementation - it turned into a 9 month implementation)

matt (RevOps Co-op)



The other service was not able to do anything they needed the system to do so they were going to have to scrap everything and start their search over, so they wouldn’t need us for at least another year.

I took the opportunity (as her CSM) ask and understand what the other system was not able to do for them, then asked if they were open to seeing more of the functionality of our system.  (they initially only needed our content not our system)

I offered to re-open her trial and gave her access to all content available, even the content she had not contracted for.

Told her I would be happy to talk to our sales leadership about letting them out of their agreement, but asked her to please take the next week to play around in our system, put us through our paces and if in 1 week we could not solve their problem we could part ways amicably.

This was on a Friday afternoon.  Monday morning, she called me happy as could be and astounded at the functionality of our system.  She asked a few questions about our development roadmap and if any bridge solutions were available to modify functionality for them.

I asked her to give me a few hours and I would call her back.  I met with the sales and development team and discussed all that had transpired and said we had a good possibility of saving this new account but we had to work together to make it happen.

We mapped out the plan with dev. and then called the customer to share what we could do in 30 days and in 60 days and that we wanted to save their business.

The best part was our system was FREE with the purchase of our content.  SO huge $$$ saver for her company.

Not only did we save the account, but they became great partners for us in beta testing changes as we worked on them. They made us a better company.

Having Sales, CS, Dev all working together to make champions of your customers is important.  Having those conversations early in the process can go along way to creating raving fans!

matt (RevOps Co-op)

that's great Christine - so my take away there is the cross functional nature work goes both direction, having sales understand the CS / implementation workflow during their training can go along way, but having CS / implementation understand the sales process is critical as well, because when you're in those "save" types of situations you are basically reselling the customer


It can’t be an Us vs Them mentality.

matt (RevOps Co-op): So we talked about trainings / onboarding and have also talked weekly cross functional meetings support this alignment....but what about the systems side of things? People and process are critical, but technology is a 3rd pillar there any role that technology can play to help support alignment between sales and Customer Success?


Of course.

Having early adoption and raving fans of the tech stack and most importantly the CRM / SFDC.  Creating a central repository for all things related to the customer/client so no one is in the dark on who the players are, conversations that have transpired and stage they are at - so vital!

Because should you win the lottery for example and never return to work (I hate using the hit by a bus analogy) those poor souls you leave there to pick up the pieces need to know what’s going on so they can continue what you started.

matt (RevOps Co-op)

haha, i like the lotto example and that makes sense, documentation and proper tracking on the systems side is key

matt (RevOps Co-op): we've got about 5 minutes left here...anything else you'd want to add to this discussion around sales and CS alignment that we haven't hit on yet?


CS and Sales should function as one unit.  Not that they need to roll to the same Dept Head, but they should have an appreciation for and basic knowledge of each others function within the organization. I would challenge those that are working in an org that does not function in this way to reach out to their peers on the other side of the table - maybe have a virtual coffee/Happy Hour and talk about the challenges they each face. Help each other figure out the best way to overcome the challenges and become partners in the business.

You don’t need leadership to force this upon you - take charge of things.  Shake the Status Quo!

matt (RevOps Co-op)

couldn't agree more Christine - thanks for dropping some knowledge on this subject for us all today, really appreciate it

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