How to Find Your Next job in Enterprise Software
Over the past year, COVID & the resulting changes in how we work have triggered reflection, leaving many thinking about what’s next. COVID was a reminder of mortality prompting employees to take time off or reconsider their current situation entirely. Many realized they weren’t making the impact they wanted, felt underappreciated, or want to grow in new ways. Pundits have coined terms like the great resignation, great reassessment, and the great reshuffle have emerged as ways to describe the record-breaking resignations in 2021.
The end of the year is a great time for reflection and planning what’s next. However, between family get-togethers & end of year deliverables, it can be hard to plan your next move in a deliberate way. I had the luxury to take some time off earlier this year before interviewing extensively and finding my next role. I want to share the factors I used in my search and some tips for how to assess them. For anyone feeling the hunger for something different in enterprise software, I hope this framework can help jumpstart your search and make the decision more approachable.
The Market
The number of enterprise tech companies has grown immensely and hiring needs have outpaced the supply of candidates. Companies are also recognizing how important employees are to long-term success. Top candidates are in a great position and have more options than ever due to the rise of remote. This has culminated in a hot market for candidates although there are risks.
Valuations have grown immensely based on the assumption that best-of-breed tech companies will continue to grow at ever increasing rates. For example, Snowflake & Datadog are expected to grow at 74% & 48% respectively as they pass $1B in annual recurring revenue (ARR). I am very optimistic about long-term opportunities powered by trends like cloud, metaverse, AI, web3, etc. However, the current funding environment means tier 2 companies are raising at tier 1 valuations and increased competition from public companies & small upstarts means commoditization is a bigger risk than ever. Joining the next disruptor offers massive opportunity but there is also a lot of fool’s gold. Deliberateness and due diligence are paramount.
My Personal Objectives:
I will lay out my personal objectives since my core criteria optimize for these objectives. Your objectives are highly personal and it’s worth interrogating what you are really looking for. Some want to spend less time working while others feel underutilized & want a challenge. Defining your objectives upfront will help you stay grounded. Here are mine:
- Long Duration Opportunity: I wanted to join an organization where I could contribute & grow for 3–5 years
- Good personal upside: I wanted my hard work to grow my skill set in building companies, have upside earning potential, and set myself up for future opportunities
- Growing my social graph: I wanted to find A-players that will challenge me and become long-term friends & mentors. I also wanted to get exposure beyond the sales function.
The Core Criteria:
Core Criteria 1: Confidence that this is or could be a market leader:
Software has never been more democratized or competitive. Consumption-based software pricing, G2/Gartner reviews, and reduced barriers to entry mean customers have more choice than ever. At the same time, software markets are becoming winner takes most and businesses need the best software to compete. Great software can reach scale quickly and the reputation of bad software can spread quickly. Bessemer Venture Partners claims that market leaders will capture 50% of the market while players 2 & 3 capture 40% and niche players capture the rest. In short, differentiation is more valuable than ever while being harder to maintain.
If you want to grow your skill set and earnings, you should aim to find a market leader or market leader in the making. Market leadership is a complete package: sales teams can no longer carry subpar products and great products can be hamstrung by ineffective sales & marketing. Market leadership is also relative: Salesforce & Hubspot both offer CRM but are leaders in different markets. Salesforce is the market leader in front office transformation and is great for end to end transformation. Hubspot has taken a leadership position in the market of low lift sales/marketing suites.
How to assess market leadership:
- What market does the company aspire to lead? Start here. It may be less obvious than you think.
- Does the category matter? Great businesses often solve important problems that are important and widespread. Solving hard problems for a broad range of customers results in massive total addressable markets (TAM). Important categories also resist commoditization because customers don’t want the second or third best solution for business critical processes. Assess this by listening to users/customers talk about their usage or talking to the target persona about the problem space. Recorded or virtual conferences are a great way to assess this. Caveat: Some amazing companies are focused by design — Workday focuses solely on the enterprise, Rippling focuses solely on SMB, and Veeva does only life sciences. All have done amazingly well and solved important problems but with limited scope.
- Analyze the data & anecdata: Analyze the company with an eye for data like user/revenue metrics, case studies, industry periodicals, or Twitter/Hackernews. Read PR releases carefully to separate facts from spin. A true market leader should be solving customer problems across multiple use cases & contexts. For startups, look for quality of adoption. As a disruptor, they should be providing unique value to early adopters. For larger organizations, analyze breadth to see if they are winning the core of the market. If the company is most successful in certain industries or segments, ask how they are thinking about the rest of the market. If their customers all look the same or the value is unclear, the company may have a limited runway.
- Is the position and/or growth sustainable? Startups have low customer counts so focus on assessing how scalable the current growth is. If the founder is required for every deal or there is a high reliance on customized professional services, dig in. For larger organizations, focus on the value customers are getting. Large organizations should provide strong cohesive value propositions. If the organization is selling a hodge podge of unrelated products or relying on financial compulsion, dig in. Ask some tough questions here, you will be glad you did.
Core Criteria 2: The company has a high performing culture
If current market position is a measure of altitude, then a high performing culture is a measure of trajectory. In the long-term, culture determines the caliber of talent the organization attracts and how effective that talent is. This will determine product velocity, clarity of message, and execution in servicing customer demand. A few hallmarks of a great culture: 1) great people 2) frameworks to help those people be successful 3) recognition and rewards so top performers can grow with the company.
How to assess culture:
- Interview process: The interview process shows how the company assesses talent. It can be tempting to think that great interview processes make us feel good. In reality, great interviews can be uncomfortable and should leave you challenged but excited. Look for exercises especially with a written component and interviewers that go a few layers deep. Your interviewers also demonstrate how effective the company is in communicating its vision. Recruiting operations can provide great signal since it is direct exposure to how the company runs. If the team does a great job coordinating and communicating, you may have a winner.
- CEO: The CEO sets the tone for the organization. They will navigate the company through challenges and make difficult decisions. You should feel confident in the CEO’s capability and judgement. CEOs are more accessible than ever via Twitter, podcasts, etc. At smaller companies, it is often possible to meet the CEO — do not pass on this opportunity.
- Track Record: Assess whether the team has a track record of setting goals and hitting them. Are they successful through intention or acts of greatness? Seek the former and avoid the latter. Sales leaders should have a track record of reliable forecasts and product teams should have a track record of shipping on time. Find a company that sets meaningful goals and generally delivers. Delivering too high or too low can indicate goals & expectations may be miscalibrated, which is detrimental in the long-run.
- Values & norms: Great cultures are intentional in who they bring on board and the behaviors they encourage/discourage. See if the company has documented values or examples of their culture (i.e. interviews or employee spotlights). Employees referencing the values in interviews is a great sign. Try to backchannel through your network or ask to meet other teams. This is somewhat subjective because you are assessing both the values and how they resonate with you. A company may value blind obedience for example — something that I would not like!
Core Criteria 3: Alignment with your skillset
The best way to grow is to find a place where you can be a force multiplier and ideally change the trajectory of the company, team, etc. It’s important to assess your skills and what value you bring to the organization you are considering. There are many exciting companies out there but some need your skills more than others. If your skills make a large impact, you will be extremely valuable and can experience tremendous upside. Thinking through this topic will give you a strong point of view to share with hiring managers.
How to assess skill /organization fit:
- Self-reflection: Start by reflecting on what your superpowers are by looking for trends in your accomplishments. Think through how you tackle problems to understand more about your approach/intuition. Think back on what previous employers did well and how that experience is valuable. You can also talk to mentors about your strengths.
- Understand Company Objectives: Dig into the company’s goals for the next few years. Start your research by looking at executive interviews or recent investor for public companies and funding rounds for private companies. In the ~6 years I spent at MuleSoft, the skills needed changed as our market share grew, the product/messaging evolved, and as we integrated into Salesforce post-acquisition. Outbound may be a key priority for some organizations while others may focus on selling new products into the existing user base.
- Find the match: Form a point of view on where you can be valuable and where you have skill gaps or opportunities to learn. This level of self-awareness should make you more confident and is impressive to hiring managers. If you can find a great fit then you and the organization will both benefit immensely, which unlocks great personal growth.
The less important factors (tiebreakers):
Compensation: I am privileged to be able to prioritize long-term results over short-term earnings. My advice is to do research on the market rate for your role but not to sweat minor differences unless the opportunities are equal on the main criteria. Great comp without market leadership is unsustainable since business success funds everything! If you lack skill or culture alignment, you may not earn the promised salary. Market leaders tend to deliver great results, good long-term earnings, and a lot of fun experiences.
Interest in the space: I believe team and potential for success trumps all. Winning with a great team is way more fun than losing even if you love the subject matter. Think of your best vacations — the people are often more important than the destination. The deepest I would go here is understanding the persona or problem space. If you have worked with marketing teams/technology in your career, back office finance may be too big of a switch.
Important disqualification factor: You may have personal constraints that supersede the other criteria. Things like short-term earnings, flexibility in location, or quality of benefits may be really important and it’s essential to get clarity and alignment on these in the interview process.
This seems like a lot. Now what?
I listed out a lot of questions that may make the process seem intimidating. In reality, your job search will look much like dating — find some companies that look interesting, start conversations, and dig into the details as you get more serious. I recommend building your criteria then casting a wide net of companies that could fit the criteria. Research only goes so far and the best data comes from meeting the team directly. Some companies exceeded my expectations and some were underwhelming. I hope you can use the above to solidify your criteria and use it to navigate the current hiring landscape. It’s worth taking the time to ask the tough questions and find the right fit.
I hope you find this helpful. If you want to chat or if this article helps you in your search, I would love to hear from you on Linkedin or Twitter.
