(Copy) 3642 - Executive Vice President of Engineering & Operations

Do you want to use radically differentiated processes to run a world-class software engineering organization? Learn more about this role.

Executive Vice President of Software Engineering & Operations

$ 800k/Year  ($ 400/Hour for 40 hours of productive work per week)  Remote Position   Long-term

We are searching for C-level executives who have built their careers starting as software developers and have progressed into executive roles over the years. You should be a seasoned executive who is already in a global leadership role.

You will be responsible for an organization of at least 1,250 people and will be expected to manage over 2,500 individual contributors. The person filling this role will be responsible for managing an engineering organization, as well as sales, marketing, and finance functions.

Crossover recruits and builds world class high performing teams to power the fastest growing portfolio of software products in the world. No other company provides the training and the opportunities to test yourself on the depth and diversity of projects that we do. All roles are location independent so you are guaranteed to work with the best in the world. Challenge yourself. Be part of the change.

As a seasoned executive with experience in a global leadership role, you will report to the Chief Operating Officer, and will also serve as a vital member of the global executive team. 

In our business, the CEO and COO of the group companies set aggressive quarterly goals for the business.  An EVP of Engineering & Operations is expected to lead the central organization towards achieving these goals.  Our management process is to set weekly targets with daily check-ins to ensure we are on track to achieving the quarterly results.

We are an organization where acquisitions of software companies is one of our primary goals. The EVP will play a major role in the acquisition of some of these organizations and may be expected to lead the transformation of any acquired company within our 90-day program.  We acquire a company a week.

Overall you will be expected to run a world-class software engineering organization using radically differentiated processes. In parallel, you will run operations across a variety of disciplines including SaaSOps, IT Ops, Support, Marketing, Sales, and Finance.  You will be expected to hire, coach, and manage 5-15 SVP level executives who will be managing global groups with our factory-like processes.

You will be expected to be an expert at aggressive goal setting. You should drive weekly productivity improvements to obtain significant levels of value at much higher levels than that which you will find in other companies. You must continuously improve the quality of your teams using our global talent sourcing. You will leverage your technical depth as a former developer and architect to set a personal standard for excellence.


A hiring event is a scheduled online event where all our relevant testing relating to a role is conducted on the same day. Submissions received during the event are graded the following week, and successful candidates notified if they have progressed to the next round which is an online interview with a Hiring Manager.


Attain continuous process improvements across multiple operations including software engineering, SaasOps, IT Ops, Support, Marketing, and Finance

Hire, coach, and manage 5-15 SVP-level executives owning a wide variety of critical business functions, but primarily focus on software engineering

Be a key contributor to our acquisition process and transform acquired companies within 3 months


Bachelor’s Degree in Computer Science is mandatory (MS or preferred)

20+ years engineering experience in a leadership role managing multiple teams across multiple products and technologies. This is a global leadership role for a seasoned executive

Proven track record running a 1,250+ person software engineering and operations organization during the last 5 years

At least 1 year of experience managing teams outside of software engineering. Other teams should include support, sales, finance

Be proficient at doing deep-dives into problem-solving with your teams and able to leverage past technical expertise in software development, quality assurance, cloud infrastructure, and automated deployments using CI/ CD tools

Spent at least 5 years in a hands-on software coding and architecture role

Managed an annual IT budget in excess of $100m

At least 1 year of experience managing an organization that makes use of IaaS, PaaS, or SaaS

An advanced level of English


As an EVP of Engineering in our organization, you will learn what it takes to handle aggressive growth where we measure success on a daily and weekly basis.

You will learn the importance of deep dives to resolve problems with your teams as well as the importance of managing your team on a daily basis against quarterly set quantifiable goals which deliver real business value.

You will learn to measure and track output and results and how to automate everything that you do. You will learn how to overcome the challenges of managing a fully remote workforce of over 1,250 people. Ultimately though, you will learn to move fast, take risks, and learn from failures.  You will never be bored.


Relevant Files and Links

Here you can find useful resources relevant to this role.

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SVP Blogs

Read an interview with Barry Jones, one of our SVPs of Engineering and Operations, to learn about this experiences with our organization.


About the Role

  • What is exciting about the role?

    This role is completely different from anything else that is being done by other people in the industry. Many executives come from large organizations such as IBM, and still, it's very hard to find someone who qualifies under our Basic Fit criteria. The critical aspect of the role is the management style the EVP will learn - this could excite some people, and turn some people off. We are managing things different than other companies and industries.

    Trilogy is a company that builds factories and the largest, most important factory we're building is the one that imports newly purchased companies into our existing factories, and this is what makes us different.

    We have a number of factories such as Engineering, Professional Services, Support and Finance. We are building another factory that will import companies into our various functional factories. One of the most exciting parts of the job is the size of it, how different it is and how big it will become. We are a billion dollar company with 5000 people, and scaling that to 50,000 people is what makes it so exciting.

  • What would an usual day for an EVP look like? What are the main activities?

    The EVP will be involved in goal reviews and goal setting with teams, coaching SVPs and VPs, management reviews with the leadership teams (CEOs) of sister companies, senior management (owner) review of goals and high priority projects. The EVP of Software Engineering and Operations will deep dive into troubled areas and projects.

    Anyone who joins any of our management roles will be required to be part of the Manager Bootcamp, where they will learn how to work with WorkSmart Pro.

    This is one of the reasons the role is so different and exciting. In order to succeed in the Manager Bootcamp, the ideal candidate will learn the WorkSmart Pro Management Methodology, and unlearn practices and processes previously learned. Techniques used in typical executive management will not work in our remote environment.

    Bootcamp will provide the EVP the opportunity to learn what it is to be a WorkSmart Pro Manager in a day to day environment. He/she will do deep dives into quality bar failures to find the root cause, creating and executing action plans.

  • In what part of the acquisition process is the EVP role involved?

    Acquisitions are made by sister companies of Trilogy, which then provide services to enable the transition of the acquired company to the Trilogy operating model and that of its sister companies. The EVP oversees the transition and participates in the due diligence phase.

  • How will the companies be split among EVPs, based on the industry/size/…? What types of companies will I be managing?

    Our organizational structure is based on assignments to a process rather than assignments to a company, a critical difference of the role. Some people are assigned to companies but the EVP's first concern will be the function they are assigned. As an agile organization, the EVP needs to understand that they may be assigned to whichever function needs the most attention once they graduate from Bootcamp.

  • Will the SVP's of functions such as Finance, Sales & Managed Services report to the EVP?

    At the moment our Factories are not meeting expectations. The EVP of Software Engineering and Operations will likely be given the function that is having the most trouble when they graduate from Bootcamp. The role requires that the EVP has a firm grasp of each function and the ability to teach how to use WorkSmart Pro in that area. Once completed, they will be given responsibilities for SVP's of other functioning teams, again providing the needed guidance and effective use of WorkSmart Pro.

  • Why are you not hiring internally? Are there any internal issues (cultural, political, etc.)?

    We are hiring internally. Our COO’s hiring policy is to promote someone internally once they are functioning in the EVP role. At present, none of our SVPs are functioning at the EVP level job, once they are and the opportunity exist, we will promote them. Our hiring is internally and externally, the model provides more options and allows us to quickly build the best team.

  • Once I'm hired and working for Trilogy, what will be the nature of my relationship with Crossover?

    Crossover is the payment and productivity platform used by 100% of Trilogy contractors (partners).

  • How many companies does Trilogy work with, and in what industries and locations? Can you explain the infrastructure of Trilogy?

    There are about 75 companies and 150 products. 95% of these companies are in the Software Industry. Trilogy supplies factory (common core) like services to software companies of different sizes - some are enterprise software, some are small and medium business software. The locations of these companies is irrelevant due to Trilogy's global 100% remote workforce.

  • What would be an example of a KPIs for the EVP?

    The standard management model for evaluating the performance of managers is through the measurement of goals on track.

    E.g. Improve customer support satisfaction rating from an NPS of 7 to 10 during Q4; that's an example of a high-level goal for EVP - normally set by a CEO of one of the sister companies. The EVP needs to break down that goal into sub-goals for which his team are responsible.

    Each function that is in the factory has a quality indicator, an internal and an external quality bar. The primary way that the EVP will be evaluated will be based on the quality of the output of the factories and processes that they are running. If their quality is great, then their KPI becomes the cost per unit of the factories that they are running. If the EVP runs a factory that produces engineering software releases, they will be evaluated on the quality of the releases they produce; if they are running a factory that does customer support, they will be evaluated on the quality of the customer support, and so on. The KPIs are the quality of what the factory the EVP is running and they will be measured on that weekly.

  • "You will be responsible for an organization of at least 1,250 people and will be expected to manage over 2,500 individual contributors

    We are looking for people that already have experience managing an organization of that size, but it varies so widely that this number became a reference. I will be evaluating people based on their ability to solve the most important problems and not by how many people they have managed.

  • Who are some of Trilogy's clients?

    British Airways, Nasa, Ford, JP Morgan, Delta Airlines, Disneyland and a number of others. We have a very diverse customer base.

    We have 50,000 customers across our 150 products, and these are some of our clients. Trilogy is building factories that support Fortune 500 customers. We support big companies and small companies as well.

  • What is the 90 day program that is described in the EVP role description?

    "We are an organization where acquisitions of software companies are one of our primary goals. The EVP will play a major role in the acquisition of some of these organizations and may be expected to lead the transformation of any acquired company within our 90-day program. We acquire a company a week."

    One of the key things that makes this job exciting is working on part or all of the process to smoothly integrate a new company. We cannot claim to be great at it right now, but we think that with continuous improvement, over time, we will get better and better and we're looking for people to help us improve our processes. Our target is that this process will last no longer than 90 days.

  • You have mentioned that decisions are sometimes made to be implemented the next day or even overnight - fast paced company. Are there any examples of such decisions?

    Any decision that is reversible is expected to be made quickly by the EVP, and immediately implemented. I would much rather have my managers make reversible decisions instantly and get new processes started then having them spend days, weeks, or months, forming a steering committee and getting all kinds of different sign offs from a bunch of different people.

  • What is the organizational structure, i.e. Manager-VP-SVP-EVP-COO and scope of responsibilities for each role?

    The EVP will have responsibilities across functions such as sales, marketing, finance, customer support, engineering, and infrastructure. He/she is expected to have 5-15 SVPs reporting to him or her.

    SW development team of a size of a pizza box: 8-10 reporting to SEM (Software Engineering Manager); 5/10/15 SEMs reporting to VP; 5/10/15 VPs reporting to SVP.

  • What are some of the tools used by Trilogy?

    WorkSmart Pro, Amazon Web Services, G suite, Salesforce, Zendesk, Jira, Zoom, Betterworks (for goal tracking), NetSuite, etc.

  • What about career progression for EVPs?

    The goal of the EVP is to replace the COO.

  • How many EVPs are there currently?

    There's been a significant turnover. There is currently one EVP and two offers out.

  • How many EVP's will be hired?

    Currently I'm trying to get a great team of 10 EVPs. Each EVP will be managing teams of 1000 or more people. We currently have about 5000 people in my group and I'd like to have 10,000 by mid 2019. I'd love to have 10 EVPs managing roughly 10 teams of 1000. We are growing that fast and doubling year over year.

  • What makes the EVP of Software Engineering and Operations a key role to the company?

    The EVP of Software Engineering and Operations positions is the key role for all of the sister companies. The EVP will have the ability to impact the companies directly as all EVP assignments will have a positive or negative impact on all of th 75 companies and 150 products.

  • What are some of the nice to haves for the position?

    Clear communication, expertise in functions that I am not an expert (e.g. finance, sales, marketing), to be very quantitative, scientific and love to talk about facts and numbers.

  • Is there any travel required for the position?

    Some traveling could be required every once in a while for trade shows or conferences. Our work model does not require traveling as it is not based on face to face or physical presence, our daily activities do not require any travel at all.

  • Who defines metrics, KPIs and reporting for teams?

    VPs, SVPs and EVPs, based on WS Pro.


About Trilogy

  • What is the company's infrastructure?

    Infrastructure is all based on AWS.
    Documentation repositories include google cloud/ Jive/ Confluence
    Individual contributors in the organization are also expected to have their own PC/laptop/MacBook.

  • Will I be acquiring companies in my role, and if so what is that process, why are you acquiring so fast and so often?

    You are not acquiring companies, you are providing services to the companies that will be acquired by sister companies. You might be involved in the acquisition process but the focus is in 90 days transformation process.

  • Why is there so much growth so fast, what does this involve?

    It involves the owner's appetite for growth :-) These Companies also believe that the organizational model which is in place also allows for economies of scale the bigger they grow. Therefore with growth, the cost per unit of output will decrease.

  • Who will be reporting directly to me? I'm assuming that 2500 will not be reporting directly to me, so why are you looking for someone that has managed that directly? What is your internal manager matrix?

    The EVP will have responsibilities across functions such as sales, marketing, finance, customer support, engineering, and infrastructure. He/she is expected to have 5-15 SVPs reporting to him or her.
    SW development team of a size of a pizza box: 8-10 reporting to SEM (Software Engineering Manager); 5/10/15 SEMs reporting to VP; 5/10/15 VPs reporting to SVP.

  • How are you able to acquire a company a week? Why does your company choose to grow at such a rapid rate of acquiring so many companies so fast instead of dedicating time to the existing companies and continue to develop the existing companies?

    A company a week is hypothetical; we had a 2018 plan of 50 companies. Trilogy and sister companies continue to develop existing companies. These companies also believe that the organizational model which is in place also allows for economies of scale the bigger they grow. Therefore with growth, the cost per unit of output will decrease.

  • How do we make money?

    Crossover: Percentage on top over every hire we get for our customers
    Trilogy and sister companies: Trilogy sister companies sell software. Ensure high customer retention with products which have an annual recurring revenue. Then cross-sell solutions and also go out and acquire new customers.
    On cross-selling solutions: Trilogy provides services to sister companies, as they grow, Trilogy grows.