Career & Feedback

Our feedback cycles, different levels of careers/roles, management, how we think about salary, internal promotions or career changes, and training and development.

We want Octopus Deploy to be not just a great place to work, but to be a great place to have come from. We know you might not stay at Octopus forever, but if you do leave, we want you to look back on your time at Octopus as a time of rapid learning, fun challenges, and professional growth. As you reflect on your career 20 years from now, Octopus should be somewhere that you remember as having had a significant, positive impact on the arc of your career.

Growing Company

As a company, we have consistently grown at 40% year over year for the past 3 years. The number of people on our team each year also grows by that rate. Exponential growth means we'll be hiring more people and needing to learn more things every year.

You, however, are a mere human 😀 You get older and gain only one year of experience each year! This leads to some observations:

  • Specialization: roles, over time, will probably become more specialized rather than more general. If one person today does 3-4 things, that role might eventually be done by 4 people who specialize in each area a few years from now. If you want to become an expert in something, this is a great place to do it.

  • Opportunities, to specialize, pioneer a new role, or to lead, will always come up. We'll always have openings for new managers or leaders.

  • Expectations: the level of performance demanded of our leaders will increase. If your team today is 6 people, in a few years it might be 30. Can you figure out how to manage a 30-person team by the time we get there?

One thing you can be sure of is that this growth will lead to changes, hopefully for the better. We'll do our best to coach and develop you as roles change and the company grows, and to prepare you for new opportunities as they arise.

Ultimately, you are the owner of your career, and there's only so much that we can do for you. So use the feedback cycles outlined in this section to make the most of your time at Octopus.

Feedback

Octopus people are learning and growing people. Octopus people actively seek feedback. Octopus people enthusiastically seek feedback that is thoughtful, timely, and directly actionable, and offer the benefit of our feedback to others. We use Radical Candor (summary, book, website, podcast) as a foundational approach to giving and receiving feedback.

We use immediate feedback, 1:1 meetings, 360 feedback, performance reviews, and public praise to offer feedback. We anchor our feedback to clear, human-friendly role descriptions we call Octopus People. Some general tips on feedback:

  • We can all do better. Ask for feedback, and take the feedback well. Leave your ego at the door. Thank people for their feedback.

  • Specific and sincere praise is surprisingly effective for the individual and the greater team.

  • Immediate, specific, actionable, and thoughtful feedback is the best.

As much as we encourage it, many people at Octopus find it hard to offer unsolicited feedback, especially if it's about something awkward. When you're talking to someone, try to always make room to ask for feedback. It will give people permission to speak what's on their mind.

We use a system called Small Improvements to manage 1:1's, performance reviews, 360's, and other types of feedback.

1:1 meetings

Working in a distributed environment has many benefits at the cost of being isolated by default. 1:1 meetings close some of that gap so you can build a trusting relationship, speak about what's on your mind, and make things better for yourself or your teammates.

1:1 meetings are at the core of our feedback loop, and everybody should be doing a 1:1 with their manager once a fortnight, or at minimum, once a month. A healthy stream of 1:1 meetings will have a feedback element woven throughout.

The 1:1 might be organized on your calendar by your manager, but it's your meeting. Before each 1:1, think about what's on your mind, and make a list of talking points, and put them in Small Improvements.

If you aren't finding your 1:1 meetings valuable, it's on you to call that out and to find ways to make them valuable.

Performance reviews

Twice a year we run a Performance Review process through Small Improvements. It will generally ask you and your manager to reflect on your contributions and performance recently, what your strengths are, and something actionable that you can take into the future.

There are two reviews:

  • The mid-year review, around May

  • The end of year review, around November

With both reviews, the focus should be on performance, coaching, and development. If you're performing well, we'll identify new challenges. If you're struggling or we're concerned, we'll make it clear, and we'll work with you on it with a goal of turning it around.

360° reviews

Three months after you start at Octopus, and then every 12 months on your anniversary at Octopus, you can ask for feedback from people of your choice using a 360° feedback cycle in Small Improvements. This is a chance to ask your teammates and people from other teams how you can improve.

Engagement survey

We also run a small survey every 6 months or so to get a pulse of how it feels to work at Octopus Deploy. It's adapted from the Gallup 12-questions survey. You can answer the survey anonymously. Paul and the senior management team review the survey results after each survey and use it to work out where to improve.

Getting bigger does not mean the company has to get worse in some way. It's important for us to grow without Octopus feeling like yet another big company, stifled by red tape and politics, and devoid of humanity. We'll try our best to keep Octopus a great place to work as we grow, but we need you to tell us when that isn't happening. Either talk to your manager, talk to Paul, or use the engagement survey anonymously to tell us when we're off track.

Levels, Seniority and Performance

Some teams at Octopus number in the dozens, while others are just a handful. As a team grows, there's usually some desire to have consistency around how we think about seniority in a role, and how we recognize performance.

We've standardized around five levels that signal somebody's mastery in a particular individual contributor role, as well as four ratings of their performance at that level. The actual set of expectations of each role can be found in our Octopus People descriptions.

Levels & titles

The five levels are reflected in your job title and will vary depending on the role, but typically look like this:

  1. Level 1: Junior <Role>

  2. Level 2: <Role>

  3. Level 3: Senior <Role>

  4. Level 4: Lead <Role>

  5. Level 5: Principal <Role>

The four performance ratings are:

  • Maturing: You're newer to the role and settling in

  • Needs Improvement: Your performance is falling a bit short of our expectations for the role, or compared to your peers. We're working with you on this.

  • Performing: You're performing at the level expected of the role. You should be at the 85th percentile in compensation for your role.

  • Exceeding: You're outperforming and probably ready for future growth

As a general rule, your title (which of the 5 levels you're in) will be public, but your performance rating will only be shared by you and your manager/management chain.

Individual Contributor vs. Manager track

Great individual contributors shouldn't need to become managers in order to progress their careers. So we've tried to have enough runway in our Individual Contributor track options that you can stay in the career of your choice for a long time.

That said, you'll probably need to get good at "people stuff" at some point, even on the individual contributor track. For example, a Lead or Principal software engineer or support engineer is unlikely to contribute much more than a Senior engineer, if they spend all of their time in their IDE or answering tickets.

As a level 4 or 5 in your role, expect to spend at least some of your time actively helping to elevate the level of the rest of your team, by knowledge sharing, mentoring, communicating, and planning work. You'll need to develop skills in influencing people, even if you don't manage anybody.

Manager salaries at Octopus are intended to be the equivalent of the level 4 or 5 of the same individual contributor track. This is because we want management at Octopus to be a separate track - not the place that all of our best individual contributors go to trade their technical skills for a PowerPoint diploma.

Management at Octopus

You'll have come across terms like VP, Director, Manager, and Team Lead at other companies. It's probably worth a moment to define how we think of them at Octopus, in case you're used to something different.

When Octopus was 10 people, there were no managers - which meant Paul kind of managed everybody, and not particularly well. As we grew, it became obvious that this wasn't going to work - people are, well, people, and Paul needed help. So a layer of management was introduced. But it took us a while to really figure out what management is for. Why do managers exist?

A manager (VP, Director, or Manager level) at Octopus Deploy is empowered and responsible for managing:

  • The ultimate results of their organization (their teams plus sub-teams). This generally means owning something that is important to the business or our customers. One way to achieve those results would be to do everything themselves, but that's probably not going to work. So a manager will typically have people on their team. Which means they are also responsible for...

  • The people on their team, which includes:

    • Sizing their team correctly to achieve the results they own (asking for increased headcount, etc.)

    • Hiring them (posting job ads, running the recruiting process, making hiring decisions within the approved headcount)

    • Performance feedback and ongoing guidance

    • Training plans and developing team members

    • Salary reviews for their team

    • Recognizing and managing underperformance

    • Handling interpersonal disputes between team members

    • Letting people go if it just isn't a good fit

As CEO, Paul Stovell is ultimately responsible for Octopus's long term growth and success. But Paul can't be across everything. And he isn't actually an expert on sales, customer success or marketing, or any of the other things the company needs to be world-class at.

To run the company, Paul has a Senior Management Team (the "SMT"). This is made up of the leaders of each of the departments outlined above. Each member of the Senior Management Team is entrusted to run some part of the business and is expected to be an expert in their area. They should have a firm understanding of what's happening in their part of the business; they should have a vision and roadmap in mind about where they're taking it, and Paul should be able to rely on their advice and leadership in that area.

Ideally, a manager at Octopus should have at least 6 and no more than 10 direct reports. If the manager’s organization is larger than this, it should be composed of other managers who are capable of doing all of the above for their sub-team. Even if other leaders in the teams exist to handle some of this load, the manager can’t be responsible for hiring/firing or salary reviews for more than 10 people.

So managers, Directors, and VP's aren't just here to do 1:1's or people stuff. At Octopus, all these managers are all ultimately responsible for some kind of result. That result might be the successful delivery of a software product, or growing revenue, or some other set of initiatives.

The difference in the titles is mostly down to responsibility and the level of support they can expect:

  • A VP (Vice President) is believed to be a world-class expert in a particular field, either demonstrated by their work at Octopus or in another company. They're responsible for actively setting goals and objectives for their part of the business. They can't expect much in the way of coaching by Paul, because by definition, Paul isn't an expert in that area, and he'd be a lousy coach - it's why we hired or promoted them! A VP means that a particular area is so important that the company needs that VP to succeed, and can't afford to wait for them to learn on the job.

  • A Director has similar responsibility and authority as a VP, but there's an expectation that it might take some time for them to learn to fully master the area. Typically, someone becomes a Director because we think they're ready to lead an area, but we know there'll be some learning along the way, and we think it's worth waiting for them to mature into the role because they have unique understanding or experiences in the company that makes it a better long-term bet than hiring somebody else. They still probably can't expect a lot of coaching from Paul.

  • A Manager also looks after a critical section of the business, but they can also expect a good deal of coaching and mentoring from their VP or Director (or senior managers), who are by definition experts in that area.

We do sometimes hire at the VP, Director, or Manager level, but in general, we've found internal promotions to always work better, so it tends to be our preference. It's not a hard and fast rule though.

Every manager and team is different, but as a default, expect to spend your time roughly like this:

  • 25% directly talking with your team - team meetings, 1:1, feedback, listening, and training sessions.

  • 25% thinking and organizing: what are the objectives, what should we improve, what's next for the team, what skills are we missing, where are we weak, what needs to be prepared in advance.

  • 25% pet projects, individual contributor work, and things that fall through the gaps and just have to be done.

  • 25% with customers, advisors, experts, people from other teams, and "managing up" - communicating and setting realistic expectations with their manager/Paul.

We encourage managers at Octopus to always keep a pet project or two where they are "on-the-tools", as it keeps their skills relevant and their imaginations grounded.

Team Leads

While managers are ultimately responsible for driving some set of results at Octopus, their team may be running multiple projects at once, and the manager may not be able to effectively spend time on all of the planning, strategy, and coordination for each project. If there are multiple people trying to plan and communicate a project, it can get confusing. So the manager may ask somebody on the team to wear the Team Lead hat for that team. Luckily, Octopus is full of experienced, smart people who have the skills to do some of that.

Being a team lead is something you do, not something you are. It might be something that you do for a few weeks on a project or something you do for a few years. A team lead might co-ordinate and organize a subteam of ~3 people, but is not a manager as described above. Think of them as individual contributors who are spending some of their time organizing, communicating, and mentoring.

A team lead might do 1:1's occasionally with their subteam, or do some mentoring, and probably has some leadership skills, but they aren't expected to act as managers. That is, they don't hire, develop, or manage underperformance in their team. As a rule of thumb, team lead time should still be 80% individual contributor work.

Anybody at level 4 or 5 in their role (e.g., a Lead X or Principal X) by definition has the mentoring, organizational, strategy, and communication skills needed to do team lead work, so it's something that we expect anybody at that level to be able to step into or out of when the company needs it. A team lead will probably be the more senior person on the team (but not always) but the team lead isn't paid any extra for acting as the team lead.

Internal Promotions or Career Changes

From time to time as Octopus grows, we'll find ourselves in need of someone to perform a specific role. Sometimes we hire externally for these roles, and sometimes an internal hire makes more sense. External hires bring outside knowledge and experience that we might not have internally. Internal hires come with all the context and history, which is hard to teach.

When we think about internal promotions, we should first differentiate two types of promotions:

  • Natural progression and mastery of your role: For example, an engineer who’s performing at a senior engineer level. These tend to be “recognition” based: we notice that someone might be doing a similar job to before, but their performance is worthy of formal recognition. There’s no limit to these kinds of promotions, they are merit-based. This is handled by our Performance Review process.

  • Promotion or role change: For example, an engineer moving to a product role, or a marketing team member asking to switch to a sales role. There tends to be a limit to how many people we can have in these roles (there needs to be an “opening”).

For any job that we're hiring for and where it makes sense to consider internal applicants (which should be all the time), we'll write a job description and invite anyone to apply. If you apply, we'll interview you and make a decision in the same way that we would for external candidates.

Applying for a new role internally, and taking on a new role, requires a leap of faith for you and for us.

If you are hired for a new role internally, it's probably because you're amazing at what you already do. The worst outcome of an internal hire would be to lose someone who is amazing at what they do because we promoted them too soon, or to a role that wasn't quite the right fit. It also means we need to find a replacement for what you already do. So this is something we'll weigh up. Internal hires nearly always work out best for us, but there's a lot to consider, so there are no guarantees.

"Acting" titles If we promote you to a management role or a completely different type of role (e.g., support to marketing), we'll often put "(Acting)" at the end of your job title. If your salary in the new role is different, it will take effect straight away.

After 3-6 months in the role, if we all agree that it's been a success, we'll remove the "(Acting)" suffix. If it doesn't work out, you can return to your previous role & salary, with no hard feelings.

Compensation Philosophy

Here's how we think about compensation at Octopus:

  • We don't offer bonuses, commissions, or stock options, as part of our "no carrot, no stick" philosophy. Your compensation is all in salary.

  • We aim for our salaries to be at or around the 85th percentile for a particular role at the "performing" level (see below) in their local market. That is, if you're meeting our expectations, you'll be paid more than 85% of people in a similar role at other companies.

  • We aim to pay competitively with companies that we feel are comparable to Octopus in their working environment and approach.

  • We aim to pay fairly: two people contributing similar value to Octopus should be paid similarly. Two people who are contributing significantly differently to Octopus should be paid differently.

We use the "printer test" to guide what we pay people: If we inadvertently shared our payroll spreadsheet with the whole company by leaving it on the printer, we can stand by it with a sound explanation as to why people get paid what they do when compared to each other and to the market.

Local market

There are plenty of reasons that we want you to feel "trapped" at Octopus: the culture, the freedom & trust in the role, the empowerment and satisfaction from your work, and so on. But the one reason we don't want you to feel trapped is for the money. If we paid far above the market, we'd create a situation in which, even if you hated working here, it would be too difficult to leave.

So, your pay at Octopus will typically be somewhat adjusted by the market you're in. At junior to mid-levels, this is likely to be the town or city that you're in. If you're a Support Engineer in Boise, Idaho, we want you to be one of the best-paid Support Engineers in Boise, Idaho.

For the same reason, we won't try to attempt to match the salaries you might get if you worked 12 hours a day at a hedge fund, or for Google in San Francisco. Our goal is to pay towards the top-end of the market for a given role, at least compared to companies you'd actually enjoy working for, and to make you feel trapped by the trust, challenges, and the great people that you work with, instead.

At top levels of a role, we know that the market for your skills can also be wider than your home town, as the number of remote jobs increases. We do factor this in when we think about your "local market".

The country you are employed in will affect your salary too, due to the local market, but also because Octopus offers different benefits and has different obligations depending on the country. So comparing salaries for the same role across countries isn't as easy as applying an exchange rate.

Salary reviews

Many people feel uncomfortable talking about their salaries or asking for a raise, so at Octopus we set up a predictable system to support you.

As explained above, we run two performance reviews a year:

  • Mid-year performance review (around May): This review is focused purely on growth and performance, and your salary is very unlikely to change at this review, except in exceptional circumstances (e.g., a Support Engineer who's clearly been performing as a Senior Support Engineer for the past 6 months).

  • End-of-year performance review (around November): We also conduct a salary review across the board at this time, review market salary data and benchmarks, and make adjustments to your salary if appropriate based on your performance and growth over the year.

It's easy to adjust your salary up when performance is good, but difficult to adjust it down, and historically we've shied away from doing that even when it's obvious that we should. Plus, it detracts from the important thing: finding ways to develop and improve. Before we increase your salary, we're looking for 5-6 months of consistent, sustained performance; not a few good weeks leading up to the performance review.

If you're unsure where you stand or you're concerned about your salary, you can always talk to your manager.

In previous years we did salary reviews once per year and simply applied a standard raise across the board. We no longer use the "standard raise" concept, as we've gotten a lot better at doing individual reviews and benchmarking, and we're confident your salary will be an accurate reflection of your long-term contribution and growth.

Progression & Compensation

As your skills increase and your contribution to Octopus grows, your compensation should too. However, it's worth understanding that within a role, the progression from Junior through to Senior, Lead, and Principal isn't a binary thing - it's a gradient because it requires demonstrating many different skills, some that you may have figured out, and some that you haven't yet.

This diagram illustrates the idea that we try to make it so that your compensation at "exceeding" will be the same as your compensation at "needs improvement" of the next most senior role:

This means that pushing for a title/seniority change isn't that important, and seeing that somebody's title within the role changed doesn't mean that their compensation did.

As an example, suppose that you are a Support Engineer (level 2), and you want to find ways to grow your contribution to the company, and your salary over time as well.

If you look at the list of things we expect from a Senior Support Engineer (level 3), there might be 10 bullet points that explain what we expect in that role. Perhaps you do 3 of them consistently, and there's 4 you've demonstrated in the past but not consistently, and there's 3 more you're working on. That's what we mean by there being a gradient. At what point do you become a Senior Support Engineer?

You could equally fall into the "Exceeding" category of Support Engineer because you're meeting everything expected of your role, plus a bit more. Or, you could fall into the "Needs Improvement" category of the Senior Support Engineer role. Whichever title you use, your compensation probably won't change immediately.

What will change my compensation then?

Consistently demonstrating mastery of the skills of all/most of the things expected from the role. Only when you're performing and then exceeding within the role will your compensation be likely to change. As a rule of thumb, that probably means meeting 80-90% of the things expected of the role consistently, but it's ultimately going to be up to your manager.

Training

Your manager is ultimately responsible for ensuring that you have the training to do your job well. Some of that will be things they look for in hiring you. Of the training you receive at Octopus, in general, we think about it using the 70-20-10 rule:

  • 70% of your training will come from on-the-job experiences

  • 20% to come from feedback and mentoring

  • 10% to come from more formal training (internal or external)

We do have a Training Program that is available for all staff. If there's a book or short online course you need, there's a budget available that you can spend to get access to it. It's easy to use - if you think something will make you more effective, go for it.

Your manager can also arrange for other kinds of training, particularly longer courses or things that are a longer-term investment. We don't have anything too solid written down about that and it's not widely used, so the best thing to do is to have a conversation with your manager.

The Training Program policy page has more details.