Head of Sales Operations

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About the role

The Head of Sales Strategy & Operations will be the CRO’s right hand person and helps drive revenue growth for Sentry through a combination of analytical rigor and execution discipline. This person will define growth objectives for Sentry’s sales-led activities (as opposed to the Product-Led portion of revenues) and design the infrastructure and the sales and success programs to deliver on these revenue objectives. This hands-on leader will manage a small team of 3-4 people initially, growing to 6-8 in the next 12 months.

In this role you will

Act like an owner of the business and autonomously identify the highest impact opportunities for growth - based on a combination of a deep understanding of Sentry’s solutions / their position in the market and rigorous analytics

Prioritize and build playbooks for identified opportunities and develop the required capabilities to execute - from account segmentation / target account definition, to sales narratives, enablement needs, and the required process & reporting changes to measure success

Continue the build-out of the GTM operating system - own territory planning, quota setting, incentive compensation, forecasting, sales analytics, etc.

Collaborate with senior leaders of Field Sales to drive annual revenue operations planning - and alignment across cross-functional businesses

Build strong working relationships with executives and key leaders across GTM teams - (e.g. product, engineering, marketing and finance) and influence the goals and priorities of stakeholders whose mission aligns with Sales & Customer Success

Move seamlessly between strategic thinking and tactical execution - with strong attention to detail and the ability to dive deep when needed

Champion the use of AI - You’ll identify ways to apply AI to make account executives, CSMs, Support and anyone facing customers more effective and productive

You’ll love this job if you

Owner mentality - from opportunity identification to sales execution. You feel accountable for delivering the number and connect the dots between analysis and execution across teams

Unquestionable ethics, integrity and business judgment -

• you share our values, and work in accordance with those values. You are the final decider for the many situations that require judgement in the role

Familiarity with Product-Led Growth - you recognize the benefits of PLG from a go-to-market productivity perspective and incorporate that into your decision-making for sales / cs- programs and processes

Fast mover / iterator - You prioritize progress over perfection

Highly analytical - you are known for incisive questions and are the first one to spot anomalies in analyses. You keep analytics as simple as possible and as sophisticated as necessary

Strong understanding of sales methodologies and processes - An ability to pick the appropriate level of implementation marrying simplicity with the needs of the business

Systems thinker - ability to take a complex problem and reduce it to its essential components

High level of empathy for the front-line sales and customer success people - playbooks and processes are designed to minimize overhead on users. Emphasis on simplicity

Excellent communicator - you understand the needs of audiences, from execs to ICs and tailors messaging accordingly

Familiarity with software development - dev tools and / or observability a huge plus

Qualifications

Bachelor’s degree required (Master’s degree is a plus)

12+ years of relevant experience in sales operations, sales systems, deal desk, or related fields

Execution-driven mindset with a focus on achieving tangible results

Proven track record of successfully driving change and optimizing processes

Strong organizational and communication skills, with a keen process orientation

Deep experience with CRM systems and a good understanding of the handover process from sales to finance

Managerial experience is required

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $240,000 to $270,000 plus a variable. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans / programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans / programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

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