What is Value Engineering?
Value engineering is a collaborative, consultative approach where businesses quantify the value their product delivers— like cost savings, revenue generation or operational efficiencies —and build a tailored business case with the customer throughout their journey with us. This approach, often employed by enterprise giants like SAP, Oracle, and Deloitte, helps balance cost, quality, and performance, ensuring both customer satisfaction and profitability.

Why It Works

A survey by MetaCX and RevenueCollective found businesses with value engineering teams reported 13% higher sales effectiveness. The approach allows AEs to price based on the value delivered, not just licenses or transactions, creating pricing power with enterprise customers. It also allows CSMs to create a case for “why” the customer bought the solution, and measure the current strength of the partnership through the lens of the value engineering models.

At Twilio, I saw the impact of value engineering firsthand through resources created to support sales and customer success teams. Some key insights I learned:

• Drives Enterprise Revenue: Value engineering acts as a free pre-sales consulting engagement, helping quantify value and build consensus across stakeholders. CSMs then piggy back off this model and continue to iterate as the relationship evolves.

• Pricing on Value: Instead of steep discounts, businesses can justify pricing by demonstrating ROI—for example, a solution that saves $1M in costs makes a $500k price tag compelling. This becomes even more compelling when the revenue generation, cost savings and operational efficiencies increase YoY.

• Strategic Fit: Growth-stage startups piloting value engineering can validate enterprise pricing and product-market fit before scaling.

How Looker’s Customer Success Team Leveraged Value Engineering

Cost Savings
Value engineering helps companies like Looker demonstrate measurable cost savings to enterprise customers by quantifying the financial impact of their solutions. For example, Looker’s data analytics platform can reduce the need for manual reporting by automating workflows, saving engineering hours and cutting down on headcount dedicated to repetitive tasks. A value engineering team would calculate these savings upfront, presenting a clear ROI for stakeholders to justify the purchase. By showing a direct correlation between adopting Looker and lowering operational costs, customer success teams can frame Looker as an essential investment rather than a discretionary tool.

Operational Efficiencies
Operational efficiencies are a critical area where value engineering shines. Looker empowers organizations by providing real-time insights that enable faster decision-making, reducing bottlenecks in processes like inventory management, sales forecasting, or marketing campaign optimization. A value engineering team might work with customers to identify inefficiencies in these workflows and build a business case for how Looker’s platform could eliminate those gaps. Customer success teams can then leverage this framework post-sale to align on KPIs and ensure the customer realizes the projected efficiencies. This proactive approach strengthens customer relationships and positions Looker as a partner in operational excellence.

Revenue Generation
Value engineering isn’t just about cutting costs or optimizing processes—it’s also a powerful driver of top-line revenue growth. With Looker, value engineers can quantify the potential uplift in revenue by helping customers leverage data insights to uncover new sales opportunities, improve customer retention, or enhance pricing strategies. For instance, a retail customer using Looker might identify high-margin product categories that should be prioritized in marketing campaigns, leading to higher sales. Customer success teams at Looker can build on this foundation by guiding customers in implementing these strategies, ensuring the promised revenue impact is achieved. This results-driven approach not only drives customer satisfaction but also creates opportunities for upselling and long-term retention.

When Should You Invest?
If you’re excelling in mid-market but struggling to close enterprise deals, value engineering could be the key to unlocking those larger accounts. While larger companies often have dedicated teams, startups can pilot value engineering initiatives to test the waters.

If you have Enterprise customers, having aligned on value models becomes the reason for a non-event renewal.

Starting a new job can be daunting. There are so many unknowns: a new manager, new processes, new products, and new colleagues. And now, with the rise of remote work, we're onboarding without ever stepping foot in an office. The grueling interview process you just went through doesn't seem so bad anymore, does it?

In this blog post, I'll show you how one empathetic leader, Akshata Mehta, revamped VMware End User Computing’s (EUC) customer success onboarding process to make it more remote-friendly along with her team. Specifically, Akshata shares how they redesigned the onboarding experience so that CSMs could organically build a support system for themselves and find safe spaces to ask questions without judgment.

Akshata has been on the customer success team at VMware for over 4.5 years. During that time, she's seen the customer success team's culture and needs shift due to the pandemic. As a passion project, Akshata set out to make the customer success onboarding experience better for new hires who were going through it remotely.

There were two key pain points that the customer success team faced when onboarding new hires remotely:

• Bridging different skill set gaps with the same onboarding process. For example, VMware hired CSMs who were either very technical or highly seasoned in customer success. The challenge was: how does the CS team customize a remote onboarding experience that enables both technical skills and soft skills? How would the program bridge both gaps simultaneously?

• The "emotional stress" aspect of remote onboarding. Akshata noticed that the culture was shifting as new hires were not in the same place as their team members. "You can't quickly tap someone on the shoulder and privately ask a question that you think might be basic," said Akshata. By onboarding remotely, new hires were unable to find their "buddies," who they could develop comfort with asking their basic questions. She wanted to provide new hires with organic avenues to create their community, especially before the flood gates open, when these new hires are given their accounts and buried in work.

With these challenges in mind, Akshata and her team planned an on-demand training program, which is a combination of both CSM job related soft skills and technical bootcamp required to get level 100 understanding of the product. The team divided onboarding into four phases:

1. Onboarding Bootcamp

2. Scheduled Shadowing

3. Mentorship Program 

4. Bridges Program

Phase 1: Onboarding Bootcamp

This phase includes the basic, run-of-the-mill aspects of onboarding. It's a three-part series that's role and organization-specific. During this phase, new CSMs learn about VMware's values, what the customer success organization looks like globally, and what their day-to-day life would look like. This phase was focused on teaching the basics of resource orchestration - which teams to engage, how, and when. This phase also includes education on tracking tools, success planning, and a list of Slack channels, etc. Akshata emphasizes the importance of laying a good foundation of the basics before moving onto the next phase.

Phase 2: Shadowing

In this second phase, new hires sign up for a four-hour slot every day for two weeks, dedicated to shadowing. During this phase, new hires shadow 10 senior members of the customer success team on customer-facing calls. Akshata describes that the key during this phase was having the onboarding team pre-select the CSMs to be shadowed and schedule the calls on behalf of the new hires. In the past, new hires were responsible for scheduling shadowing calls and pinging their peers, which can be a daunting task that doesn't always lead to shadowing.

During this phase, new hires are asked to do two specific tasks:

• Observe the different styles of each CSM and build a list of takeaways. The ability to compare 10 different people in how they approach challenges and achieve outcomes allows new hires to envision themselves with a particular style so they can adopt it.

• Opportunity to build relationships: Akshata hoped that exposing new hires to 10 CSMs would allow them to meet with different CSM’s outside of their direct team and ice breaker conversations with them. This would help build a relationship with them, where they would be comfortable enough to ping them for help. "If you like the way this CSM you're shadowing builds success plans, or responds to customers, you're naturally inclined to make an effort to build a relationship with that CSM so they can help you in the future. The goal here is to inspire and motivate new hires to build relationships with senior members of the team that aligns with their specific working style," said Akshata.

Phase 3: Mentorship Program

At VMware, there are multiple customer success teams that align with different products. When everyone was in the office, it was easy for new hires to meet CSMs from different teams, run into them, or grab coffee with them.  She wanted to find a way to rekindle that organic networking experience. 

So, during this phase, the new hires venture outside their customer success team, to a sister  customer success team.  “The goal is to bolster the new hire experience and provide an alternative perspective outside the new hire’s direct team”, says Akshata. This program is designed to be 6 months long, but can extend beyond this period, and the time commitment is 2 hours a month. 

The hope from this program is it would enable the new hire’s professional growth and allow them to grow their network, while also tackling new experiences in the workplace. This is a second avenue for new hires to build trusted relationships and be a part of the VMware customer success community. Akshata perceived the mentorship program as yet again, another opportunity to network that hopefully allows the new hire to not feel disconnected during the onboarding process. 

Akshata found a unique way of matching CSMs, kind of like a dating app. “We match them based on common traits such as being a recent grad, industry experience, time zones or even based off the same city”. 

Phase 4: Bridges program: This program runs in parallel to the mentorship program. Once new hires are assigned accounts, this program helps bridge the gap between onboarding and account management. The bridges program provides the new hires with yet another avenue to interact with the recent hires (before them) via a Slack channel, join a bi-weekly call where the veterans would either have a SME talk, a forum discussion or even just a happy hour for mingling. specific slack channel that includes 2 veteran CSMs, and the rest are new and recent hires. “These 2 veterans  & recent hires in the slack channel answer all new hire questions. The goal is to create a safe space for the CSMs to ask whatever they want, ask the same question multiple times, or whatever they need”. 

Continuous improvement: Akshata wanted to ensure that this is an iterative, evolving program that continues to serve new hires better. To do this, the team has a feedback form specifically designed for mid-term and end of mentoring period. Based on the feedback on timeline, cadence, and how to enhance the program, Akshata and team continuously evolved the mentor program. 

IMPACT: The ultimate goal of any onboarding is to make the new hire ‘feel at home’ with their new company, team and role.

 By giving new hires multiple avenues to connect with their team members, having a manager and a mentor as a go-to and a safe environment to harness the knowledge from the recent new hires & veterans aims to do exactly that. 

The hope is that this plays a good role in making the new hires a part of the community and not feel isolated in this remote world, hence improving the happiness quotient and retention. 

I hope this blog inspired you to identify gaps in your onboarding journey and suggest some of these changes. I also hope this blog provides perspective on what a good onboarding experience looks like, so you can ask for these things the next time you’re at a new company.

Sales can be rough. I should know. That’s why so many of us make the switch into customer success. In this interview, Santhi Vinnakota shares her blueprint for switching from sales into customer success. She shares her reasons for making the switch, the highs and the lows she experienced while trying, and advice on leveraging transferable skills. 

About Santhi

Santhi started her career in sales at Nutanix before becoming an Account Executive at Kustomer and then DataMinr. She didn’t love sales, so she enrolled in an MBA program to help set up a career transition, eventually deciding she wanted to transition into customer success. Today, Santhi is a Customer Success Architect at Mixpanel. 

Aisha: Santhi, why did you want to switch Customer Success?

Santhi: What I liked about being in sales was that it was a customer facing role. I liked presenting the product and liked solving challenges, drawing out a roadmap for how the product can relieve pain points.

What I didn't like was that it was a high pressure role, and being successful in it was sometimes out of my control. There were highs, like big commission checks. But the lows were just as strong and I didnt have control over them. In sales, you have to be comfortable grinding through the drudge of sales. The cold calls, sending the same email to prospects, every single day, knowing that neither I, nor the person receiving the email, cared about the message. The role was contrived, it was all about the numbers on the board. 

I craved  intellectual stimulation. My STEM education meant I was partial to critical thinking and logic based problem solving, areas that can be lacking in a traditional account executive role. It wasn't as stimulating, and I caught myself craving more of that when I was an account executive. 

The culture of most sales teams presented another compelling reason to make a change. In many instances, I was the only woman of color in the room and sometimes, the only woman in the room. Within my team, our personalities didn’t mesh. Back in the day, when we were all in the office 5 days a week, the sales floor was dominated by aggro, alpha dog men, and I didnt see myself fit within the team. I knew I needed to do something else.

Santhi clarified that the culture, stimulation aspect and the monotony in the role isn't always a problem, that all AE roles differ. These were merely components of the role she didn't enjoy. 

Aisha: So where did you start when you made up your mind that you wanted to exit sales?

Santhi: I wanted to pick the right company before I set out to change my career. I started getting closer to the product, understanding the nuances, going deeper than the sales pitch. I wanted to understand “what am I selling?” “Is this something I'm excited about?” This helped me pick some companies I knew I believed in. This is why I specifically picked Mixpanel. It's a product analytics tool that helps people answer questions about their end user, and that's the direction I wanted to go in. 

But before I landed a job at Mixpanel, I had to go through many, many customer success interviews. I was getting lots of interviews and making it to the final round. But I couldn't get an offer. This went on for quite some time. I was blowing through the interviews with my charm, but the reason why I wasn't landing an offer was because I was not spending time understanding what that specific customer success team actually does. This was the lost key. Customer success is a murky world. Sometimes it's professional-services-heavy, sometimes it's playing quarterback, sometimes it's an expansion focused role.  I didn't spend enough time understanding how each team was structured, and what their specific needs were.

Santhi went on to describe how the right company will make the customer success role enjoy-able and emphasized the importance of doing due diligence on the needs of the team, and how they are a match for your skillset. She advised on making a list of the needs of the team and matching each item of that list to your strengths, if there are any visible ones. 

Aisha: It sounds like picking the right company is a very important part of making the switch. How should one go about picking the right company to do customer success for?

Santhi: When I was an AE at Dataminr, I started with interviewing their customer success team to get a better understanding of the role, which served as a great starting point. What I learned there was that their CS team was focused on expansion and renewals, less retention and adoption plays and that wasnt of interest to me. 

Another nuance to notice is the complexity of the product, while making your decision. Is it a plug and play product? Or is it complex and very technical to onboard? Pay attention to who the end user is and how they’re using the product. Is it easy to set up, or is there a long implementation cycle? Plug and play products that don't require as much customization can lead to simpler implementations, which means down the road, customer success does not play as big of a role in adoption. For the more complex products, your customers are going to come to you, the CSM, to help them learn how to use the product, how to set up the product. That's where customer success tends to play a larger role. 

Another simple way to learn about the company is to read the case studies. These case studies are often written by customer success managers, or the CSMs gather information for the marketing team to write the case study. By reading case studies, you’re killing two birds with one stone, you’re learning about the product and how CSMs position it. 

Aisha: Now let's get to the meat of this conversation- What are some transferable skills from sales to customer success that AE should highlight as strengths for the CS role?

Santhi: 

1. Make the switch internally: Switching roles within the company is a great option because you are a known quantity. People know what it's like to work with you and can envision your strengths to work in your favor in the new role. 

2. Choose a company in the same industry: If you’re switching roles, one of your strengths can be that you’re well versed in a particular industry. For example, if you’re in martech and specifically analytics, stick to analytics companies. You understand the language, the problems, and have dealt with similar challenges. 

3. Multi- Threaded: Both AEs and CSMs need to be multi-threaded in an account. You have to talk to the product team like a product manager and at the same time, sell to executives on the dollars, because they don't care how the black box works, as long as it's bringing in revenue or helping cut costs. In your interviews, be sure to highlight how you can be a chameleon!

4. Resource Coordination: During a complex sales process, The AE is the quarterback bringing legal, product, engineering teams into the deal. They lead and create proof of concepts, SOWs. CSMs are similarly the quarterbacks after a deal closes.

5. Customers Success role with expansion built into their variable: Customer Success compensation comes in all shapes and sizes. Sometimes variable compensation for CS roles is based on a team goal, and sometimes it's based on expansion targets. Look for roles where expansion is baked into the customer success role through variable comp. The hiring managers are actively looking for sellers. 

6. Customer facing experience: One highly effective transferable skill is, unsurprisingly, having customer facing experience. I emphasized how I handled complicated situations with massive pain points and drew a roadmap for how we could solve them. 

7. Building Trust: Enterprise sales cycles are months long, and as an AE, you have to be savvy enough to play the role of a trusted advisor, and avoid coming across like the money guy. AEs are also very good at salvaging situations, which is a valued skill in customer success. 

8. Executive Relationships: Another skill that's highly transferable is the ability to build and maintain executive relationships though the long sales cycle. Think about how you kept executives interested and how to manage their expectations in a long cycle. This skill directly applies to CS roles. AEs maintain these relationships post sales, and this is where CSMs and AEs collaborate in fostering the executive relationship. 

Making the switch to customer success isn't easy, but is definitely do-able. I hope hearing about Santhi’s experience gave you insight into what the process looks like and how to play into your strengths to make a good case for why people should hire you as their CSM. 

2023 has already seen many layoffs at companies like Meta, Salesforce and Yahoo.

We're seeing an unprecedented time where some companies in the Martech space have cut most or all of their customer success team. And more are likely ahead, so it’s a great time to brush up on your interviewing skills. In this blog, we’ll talk about what managers at Unicorns like Iterable look for when hiring top customer success talent and the components make up a customer success role. 

About Tasmin 

I sat down with Tasmin Singh, who manages an Enterprise Customer Success team at Iterable, one of the leading cross-channel marketing automation platforms in the marketing technology (Marctech) space. We asked Tasmin to spill the tea on what she looks for when interviewing candidates, and she's not one to gate keep. 🙂

Tasmin has been in Martech for over a decade and while she leads a Customer Success team now, each role leading up to where she is now has been what she calls “a 30 degree pivot.” She began her career as a Data Analyst for cross-channel marketing campaigns at Yahoo!, pivoting to a Mobile Developer Evangelist role at Flurry Analytics. She describes the evangelist role as “customer success light” since her focus was on engaging and retaining customers on a free product. 

Her first traditional role in Customer Success was at Localytics (a mobile analytics and messaging platform), where we worked together!  

After that, Tasmin joined Iterable as an Enterprise CSM, and fairly quickly, got promoted to an enterprise team lead, where she now manages a team of 7. Since she joined 4 years ago, Iterable has grown from 200 to over 700 people and most notably the CSM team went from 10 people then to 70 and counting now.

Aisha: Every team structures their Customer Success team differently. Some businesses have dedicated Account Manager, Solutions Architect, and a Customer Success Manager, whereas Iterable hires Full Stack CSMs. Can you share a bit more about what it means to be a Full Stack CSM?

Tasmin: Iterable’s customer success team sets the bar very high when interviewing and we look for “full stack CSMs”.  A full stack CSM is a blended role between revenue, strategy and technology. In terms of sales experience, we look for CSMs who have experience with contract negotiations and renewals. 

Aisha: That’s so important. I’ve learned that this is a critical thing I need to ask before interviewing somewhere, so I know what type of support I’ll have and what I’ll be expected to handle myself. What else do you look for in a Full Stack CSM? 

Tasmin: On the strategy side, the obvious things we look for is the ability to conduct business reviews, create mutual success plans, ability to assess usage metrics to create adoption plans, devise and present use cases to unlock, but strategy is more than these basics.

We value CSMs who can provide customers with guidance and best practices. For example, one of the biggest challenges facing marketers today is stricter privacy rules that make measuring performance marketing harder. So we look for CSMs who have experience helping customers overcome these challenges. This means folks who are coming from the martech industry who are familiar with recent privacy changes with ATT (App Tracking Transparency), GDPR, deliverability changes, BAAs, etc. If the candidate is able to describe a scenario in which they provided a high level strategy, this is a good indicator that they are aware of industry trends.

I’ve also seen CSMs who try to tackle everything alone, and end up failing to deliver customer outcomes. So I look for candidates who know when to bring in our Professional Services or Solutions teams. We call these resource coordination skills: the ability to draw a line in the sand where CS expertise ends and the need to bring in other teams to solve a customer problem begins. 

Lastly, we evaluate technical expertise. Now let me be clear, we don't expect that everyone is going to be an engineer. This is why resource coordination is an important part of the role. But some candidates don’t have the technical depth to ask the right questions. So I look for folks who are familiar-enough with the language and the product to know when to bring in a Solutions Architect, and how to articulate the problem at hand. We call this gathering technical requirements, the ability to frame the technical issue. 

I also want to note here that we don't expect every candidate to be strong at all three. We prioritize one skill over the other based on what the team is missing at that time. For example, someone might be great technically, but not good at contracts. If the team has many technical people and just a few negotiators, we might pass. My advice would be: ask the hiring manager what is important to them or what the team is prioritizing, and be open about your strengths. 

Aisha: What do you look for when you are Interviewing candidates? 

Tasmin: 

1. Resource allocation skills: Since we were on the topic - Understanding and executing resource coordination is key, especially on the enterprise side. We’re not looking for experts because Iterable has made it more nuanced overtime, we have a handbook with scenarios. 

2. Company Values: When we do peer interviews, we generally have each candidate focus on one core competency for the role and one core company values (in Iterable’s case those are Trust, Humility, Balance, and Growth Mindset). Doing so allows us to avoid redundancies in the questions you are asked but also gives us some breadth and depth into your background. This is an increasingly common practice for larger companies so I recommend spending some time on the company’s page to understand what their values are and how you’ve displayed those in your own career or life.

These kinds of questions can run from “what is something you’re proud of personally or professionally” to “what was your last professional development investment and how has it helped you grow” to “how do you build trust with a customer.”   

3. Strategic/industry experience: My advice here would be to know and practice your key customer stories that you want to tell. For example, anyone who has worked in customer success should be able to tell a story about a time they had to give a customer bad news and how they turned around a poor customer relationship. We need to know that we could put you in front of a $3M customer and you’d be able to build the right relationships and articulate their business needs. If it’s an industry that’s less familiar to you, make an extra effort to learn the language of that industry and its trends. 

You don’t have to have a strictly CSM background for me to hire you but do need to show me that you excel in communication, problem solving, escalation management, and proactively thinking about customer expansion. For folks who are considering a full scale pivot into to a CSM role, my #1 recommendation is to look for a CS role that serves your current industry since you will understand what that industry’s customers’ needs are and allow you to speak their language; it’s the superpower that will make you uniquely suited for those roles! 

4. Research what the company does:  I like to assess when people have done their research about our company as well as if they are able to describe their current company.

In a phone screen I will usually ask “how does your company make money?” and in a later stage interview, I will ask “Can you explain what you think Iterable’s product does?”  

It is shocking how many people come into an interview not being able to answer these questions. If you didn't take 5 seconds to google our company or are unable to articulate your company’s business model, no matter how prepared you are otherwise, I’m almost always going to pass on you. The reason is that because at the core of it, the CSM role is about knowing your customer, understanding their business model, and how to tailor your strategic initiatives with them and not knowing these answers shakes my confidence that you would do those things in a customer setting. 

A couple of sentences will usually suffice, but the candidates that have stuck out to me have gone above and beyond and will do things like citing case studies on our site, mentioning trends they’ve noticed (positive and negative) in our reviews on G2, or comment on nuggets they’ve found on our knowledge base.  

Aisha: What is the # 1 piece of advice you’d give to new and aspiring Senior CSMs?

Tasmin: Do your research about the company that you’re interviewing for (clearly I have strong feelings about this haha) and ask insightful questions during an interview. If you aren’t asking me any questions during an interview, that is generally a bad sign. That being said, please do not ask me what a typical day in the life looks like! It’s a boring question that doesn’t add much on either side. Understanding what your future managers and peers are goaled on, what business challenges and triumphs that have come up recently or are expected for the next year, how the team is structured and how your role fits in, and how you can best add value are all much more interesting for both parties and shows you’re thinking about the kinds of things I want a CSM asking their customers.

To answer this question, I spoke to Karla Abea. Karla is an Enterprise CSM at Twilio Segment and in her 7.5 years in customer success, she's worked for unicorns like Amplitude and AppsFlyer.  She shared examples of how to evaluate an employer’s strategy, product-market fit, and red flags to lookout for. 

Aisha: How do you tell the difference between a good product and a bad product, and what kind of impact does that have on a company?

Karla: I think a good way to approach this question is to talk about signals of a company set up to build a good product. In earlier stages it’s definitely a good sign for the Product team to be hungry to learn how the customer is using the product, interviewing them, perhaps even establishing a formal Customer Advisory program. A siloed Product team that isn’t asking questions can be a red flag. 

To vet for this specifically, I’d ask what the processes are that inform product direction, and the role that the CSM plays. I’d also ask what informs Customer Success goals. I find that some of the best mid-stage startups who have figured out product market fit and defined their vision, have also defined their strategy and are recruiting various teams across the org to support those strategies. While I was at Amplitude, for example, they defined their North Star Metric. It was a metric by which Amplitude measured that customers were getting value from their product, align on the definition of "value," and help them steer clear from vanity metrics. If a customer was increasingly getting value from Amplitude, their measure of the North Star Metric would increase. So we as CSMs could also measure the impact of our work based on this value, and we were aligned on what "good" looked like. So goals should be informed by a clear vision and strategy.

Another approach is to take a look at what’s being written about them by folks like Gartner and on sites like G2Crowd, as well as on app marketplaces like the Hubspot and Salesforce App Marketplace. Listen for if the same issues are coming up year after year, or if the product team seems to be responsive to feedback. Look for the reviews written by power-uses and pay attention to their feedback.

Aisha: You’ve worked at 6-person startups, 60-person scale-ups, and a 6000 person unicorn: how would you contrast them, and what type of person will succeed in each? 

Karla:

Early-Stage (6-Person) 

At a 6 person company, the teams are leaner with everyone wearing a lot of hats. You’re part of creating lots of processes, from how to support customers, to how to triage bugs/unexpected behavior. You’re learning a lot about the customer's pains not just directly related to the product but sort of in the periphery of the product as well. So, as a CSM, you end up playing Product Manager, Product Marketing Manager and Solutions Architect. 

Another benefit of an early-stage startup is you have tremendous visibility: you’re at the forefront of learning from the customer and helping leadership translate that into the next iteration of the product. You get to see the product built first-hand. 

Are you comfortable with ambiguity? At a startup, you’ll be developing processes as you go, doing things that don’t scale. And shifting directions. Are you okay with this?

You also must be comfortable working independently with minimal guidance. Ask yourself: is being scrappy your strength? Or do you hate hitting a wall? 

The most important part is to be comfortable with the company not going anywhere, while keeping your own interests in mind. I once worked for a company that fired 2 rounds of sales teams, after which our CEO became the interim sales guy. "Eventually I became dissatisfied with the lack of growth. That’s when I knew it was time to call it quits. 

Growth-Stage (60-Person) 

Culture

A 60 person company is different. Rather than building processes, you’re plugging into existing processes, but you still have some authority to improve them. New roles get created and new offices may be established, so it’s an exciting time. 

There are challenges, too.  In one case, as we started preparing for an IPO, we started bringing in bigger-hitters. That was exciting, but as the culture started to shift, it was rough for the more tenured folks. These types of cultural shifts are inevitable, and can be a huge opportunity for the team members who want to grow along this new phase of the company -- not everyone does, and that's okay.

Discovery

At the growth-stage, the leadership team should understand where the product fits in the market, the pain the product addresses. They should have a vision for where they want to take the product. As a CSM at this stage, you’re still educating the customer a lot on your product and how it’s solving their pains, or how they have pains they didn’t even realize could be alleviated by something. This is especially true for category creators. People don't recognize they have a pain, or what the pain represents. Customers need education on their pain. The CSMs who succeed at this stage are excellent at discovery, and attaching pain points to a product. So, if BANT is your strength, a 60 person company may be a good fit.

Strategy

At this stage, scale-ups also start to work toward moving upmarket from SMB to Mid-Market to Enterprise. So as a CSM, if that’s of interest to you, then it’s a great opportunity to contribute to and operationalize how the company can support bigger and more strategic customers. 

Late Stage (6000-Person) 

A 6000 person company is likely to post-IPO. Processes are much more formalized, and the start up mentality may be waning. The company is now a serious player in the industry and wants to recruit the skills that reinforces this status. You may still be cementing your move upmarket, so growing those lands becomes a much bigger part of the growth strategy. 

Unlike early stage startups, you’re not wearing many hats and your role is becoming more specialized. If you’re a strong seller, then you might look for opportunities to work on bigger accounts or those with more growth potential. If the account has multiple subsidiaries, then CSMs who have more experience with stakeholder management are a natural fit. These accounts have lots of cooks in the kitchen, lots of coordination between different departments. You’re moving away from customer education and enablement. So if you love people management, and keeping stakeholders (internal and external) aligned, this may be a good fit for you. 

Aisha: What are some early stage company red flags? What questions did you ask the CEO of the 6 person company?

Karla: To be honest, I didn’t know what to ask back then! 

One thing that’s not a red flag: an early stage startup that doesn’t have everything figured out. These present really great learning opportunities so long as you’re hungry and curious and willing to think outside the box. 

Though in retrospect the 6 person startup I worked at wasn’t hugely successful, it was a great stepping-stone for me. I got to wear a lot of hats that ultimately helped me form my own philosophy about the CSM role.

One red flag I wish I had known to look out for: lots of team attrition. Another is negative customer reviews for the product on blogs, Reddit. There may not be much written about them on G2Crowd or in Gartner Magic Quadrants,, but what those early-adopters are saying is a good signal about P-M fit. 

Overall, early-stage offers CSMs a lot of influence and a lot of opportunities to make a big impact.

Choosing the right company for your skillset and your growth is a daunting decision, and I hope you can apply some of this advice on your decision making. My goal was to provide you with practical, insightful tips on how to choose your next role. Good luck in choosing your future endeavors, friends!

So how do you create mindshare with a customer’s executive team? Frequent Executive Engagement.

To learn about how to better engage with execs, we interviewed Tara Sharma, an Enterprise Customer Success Manager at Twilio Segment. Tara graduated from London Business School in 2020 with an MBA. Prior to her stint in London, Tara worked at Qualtrics as a Senior CSM and also worked at KPMG as a management consultant. What makes Tara an exceptional wizard at her craft is her consulting and MBA experience, specifically in strategy and operations. 

People with backgrounds similar to Tara’s typically traditionally sought roles in areas like product marketing, strategy & operations, or business development. But recently, there’s been a noticeable push to bring people like Tara into customer success. When working with large enterprises, their needs are complex and unique. So hiring post-MBA candidates with more traditional corporate backgrounds like consulting brings much-needed structure and frameworks to customer success.  

Aisha: Tara, thanks so much for making time to teach us about how you conduct Executive Business Reviews. Let's start with the basics - why do you use Executive Business Reviews? Why do they matter? 

Tara: An executive business review takes place between executives on both the customer and the vendor side. The purpose of these meetings is to maintain executive alignment on both sides, educate and keep customer executives informed on the value of the partnership. This ensures continuity of the relationship and allows us, as CSMs and as an organization, to reset expectations when needed. Think of an EBR as a tool to facilitate effective communication, to  highlight things that allow for the customer to become a strategic partner. When it comes to enterprise accounts where a CSM is working with 15-20 different products across multiple teams, EBRs are leveraged as a tool to facilitate communication across the different teams and bring them together to review the larger, more macro goals of the business. Especially, in SAAS, where customers are working with multiple vendors, we use EBRs as a tool to be seen as a strategic partner, not just another vendor. 

So again, the objective is to maintain executive connection, to ensure alignment on high level business initiatives, raise and address risk on both sides for effective mitigation. 

Aisha: When is a good time to conduct an EBR? What are some “triggers” that should point into the direction of an EBR being due?

Tara: One of the main reasons to have an EBR is to have tough conversations and elevate the conversation to the right people in the organization who care enough to solve the issue, on both the customer side and our side. Outside of EBRs, we meet with customers on a regular basis, where we focus on achieving daily goals. During EBRs, you have the opportunity to step back from the day to day, look at the partnership holistically and call out what's working, and what's not working. As an individual contributor on a project, an EBR is an opportunity to highlight blockers and ask the executives for buy-in, or help in solving for these blockers. This goes both ways, where us as CSMs can ask the customer executive for their assistance and understanding in solving for the blocker and aligning resources internally to solve for the blocker.

Another way to use an EBR is when you achieve a key success in the partnership that you want to brief the executives on. This is not just an opportunity for us as CSMs to highlight our achievements, it’s also an opportunity for individuals on the client side to showcase their successes. Especially for larger, enterprise customers, where you are working multiple workstreams at a time, I don't think that we take enough time to stop and look at our work holistically, and take the time to quantify the value of the day to day work. 

You want to present these key successes to people a few levels above your program manager; i.e. the VPs and C-level executives. When you present the key successes to the right executives and once they become aware of the use cases or revenue being unlocked, they are able to provide further guidance on what to work on next. EBRs can be inspirational and get executives talking about the drivers of the partnership. 

An EBR is also a great opportunity to land and expand into an enterprise account. When you are showcasing a big win at an EBR, this can be an opportunity for your AE to create an expansion model by asking if other teams are interested in replicating this success. Work with your AE to uncover expansion opportunities and look for teams where the same model can be replicated. 

Aisha: Now let's shift to the anatomy of an EBR. How should CSMs be thinking about the content of the EBR itself? Where do I start?

Tara: The key ingredient to an EBR is cross functional collaboration. Typically, with strategic customers, you have representation from different groups as well as representation from product, engineering, support, and sales on your side. The key to an EBR is to collect highlights from all the different groups on the customer side, as well as teams on your side, and synthesize these into a story. You want to expose executives on both sides to your achievements and tell a story about what all the activities mean and where we are headed in the partnership. 

As a csm, be the quarterback of creating the narrative, put the pieces together, and try not to create the narrative yourself. Ask each team for their version of the story. Ask them questions like “what were the activities this quarter and why do you think they’re valuable”. Don't try to boil the ocean. Instead, gather pieces and stitch together a story. CSMs are not technical experts, we won’t always have in-depth knowledge of what each team is doing and can't always speak to these technical workstreams. It's each team’s responsibility to represent their successes, but it’s the CSMs job to look at each activity through the lens of enterprise value. 

Aisha: What are 4 things to include in an EBR?

Tara: The 4 things to cross check in your EBRs are:

1. Identifying and Preparing the narrative: Gather the pieces and craft a story. Get everyone on board. Prepare the teams to present,  iterate on the slides until everyone is aligned on the narrative. Customer execs want to hear from our execs, so prepare a talk track for them. 

2. Prepare your execs for the tough conversations: If there's something you want to highlight in the EBR that is a blocker and your team needs help, get your executives on board. 

3. Hold the customer accountable and have a move-forward plan. You had the EBR, now what? You have to continue having EBRs, facilitate communication between execs and report on progress or resolution frequently.

4. Aligning at the right level by seniority: If there are VPs from the customer side,  make sure that there is at least someone VP level or above coming from your side.  

Aisha: Are there any tips you can share on how to prepare for an EBR?

Tara:  Yes! Here are some things to think about as you prepare for an EBR

Hope you enjoyed learning about how you can add EBRs to your toolkit. Try one out on your own and let me know how it goes!