What framework do you use when assessing a new opportunity at a different company?

The most important things to consider when assessing a new opportunity with a different company are:

• The company's trajectory. Is there a viable path to success for the organization, and are you comfortable with that path? (i.e. are they profitable? If not, what level of ambiguity works for you?)
• The definition of Customer Success at the company. With Customer Success being a relatively new field, the term can be used in a lot of different ways. It's really important to make sure the company's definition of CS lines up with yours. 
• The company's definition of success in the role and as an organization. What metrics do they use? What does "good" look like?

Product: Is the product something I will be excited about? Ultimately, a CSM's role is to drive value through Product. If you are not convinced about the impact of the product, how will you convince others?

Process: Are there tools and processes in place for the CS organization? Do they have a CCO or is CS under Sales, CFO, COO or Support? Having a CCO indicates that the CEO truly cares about CS and is invested long-term in the CS organization.

Tools: Do I have the tools to do my job well? Do they have a CS solution or have they cobbled together a CS solution using Spreadsheets, chats and evernote? Just as you can't ask a legit sales rep to do their job without a CRM, you can't expect a CSM to deliver without a proper platform in place. Note, if this is a super early-stage startup, there will be no tooling and it is okay. However, it is a legitimate question to ask during your interview would be if they eventually plan to buy a CS platform.

People: Your immediate leadership makes or breaks your experience in a company. What is their leadership style? Does it align with you? Do they exhibit empathy? Do they have a high bar but also provide high support? Ask your interviewers about their most hairy problems, how do they support their teams, and what the training and ramp-up program looks like. If you don't get a good answer, run!

Business Model. For me the company should be a SaaS based company. I.e. selling cloud-based software for a subscription fee. If the company is hybrid i.e. has some older products that are still perpetual / on prem but mostly moving to SaaS then that is for the most part acceptable. Is the company's philosophy and strategy of Customer Success aligned with my own. I would also assess the maturity level of the Customer Success Organization and where it reports into. Ideally Customer Success reports to the Chief Customer Officer who in turn reports to the CEO

Business Performance and Potential. Is it a high growth company? Is the NRR in lines with industry expectations? Does the company have low churn? Are they the market leader in their field (Gartner Magic Quadrant, Forrester Wave). Is it Customer Led Growth? Are they #1 or #2 is their chosen market(s). Is the company profitable? Are they hiring & retaining staff (in particular in customer success).

I also weigh up the pros and cons of the company being publicly traded versus privately owned.

The role: Is the role both a challenging one and one where I can add value. Is there opportunity for growth and development? Will I be enabled for success? Is it clear what success looks like for the role. 

Company Values: Are the company values aligned with my own? Can I add to the company culture? How is the company perceived an an employer (feedback from connection, reviews on indeed and glassdoor)

Management & Leadership: Is the hiring manager (& next level manager) someone that I can connect with and have strong rapport. Can we work effectively together? Can I potentially work well with my Team One (Peers)? I examine the leadership and look at their past track records. Are they successful in building and growing companies? 

If you enjoy what you do and why you do it, you’ll do it better and you’ll do better. Here are some questions to ask yourself when consider a new role:

1. Do I feel good about what I would be doing in this role? Do I feel good about the company I would be working for? Maybe it’s in an industry that you’re interested in, or maybe it’s something that helps shape the sort of world you want to live in - whatever it is, make sure you feel good about it. If you believe in the company you are working for, you will have much more energy at work and in your life. 

2. Can you feel good about who you’re working with? What are the leaders and peers at the company like? Did you feel good during the interview cycle? Do the publicly stated values of the company align with yours? You’re going to spend a lot of time with these people and it needs to feel like a good fit.

3. What is the product like? If the product is weak, CSMs, almost more than any other role, are exposed to this. Will you be spending most of your time dealing with product issues to retain your customers, or will you have a chance to be more strategic? An early or imperfect product is fine, but I would try to validate what the short to medium term prospects are. Is the company early-stage and rapidly improving the product or is the product imperfect because it’s not being invested in properly?

4. What are the business prospects like? What is the industry or business space like? Is the industry growing or are its best days in the past? It can be very hard to retain your customers if there are macro economic issues at play.