Remote Second In Command Pilot Jobs in Santa Clara, CA

ABOUT SORTLY

Sortly is a simple, multi-device inventory management solution. Our visual & intuitive approach to inventory enables thousands of SMBs and teams within iconic corporations, government entities, music bands & sports teams to stay on top of their consumables, assets, and material things. With over 8,000 five-star ratings in the App Store and a net promoter score greater than 55, our impressive growth has primarily been driven by organic sources and word of mouth. We are profitable, financially independent, and primed to scale within our $20B market! We are proudly a distributed and remote-first company since inception with teams across 4 countries.

OUR VALUES

Real — We lead with authenticity, show transparency through being honest and clear, and take accountability by owning our actions and outcomes.

Inspiring — We think big, empower others to achieve their best, and celebrate wins by recognizing large and small contributions.

Smart — We demonstrate First Principles thinking by always asking "why" and seek to understand deeply, embrace growth mindset and drive decisions with data.

Empathetic — We are humble and listen with an open mind, show up mentally and emotionally to make others feel valued, and consider how our actions impact others.

ABOUT THE ROLE

The Principal Revenue Operations is a senior leadership role at the center of Sortly's go-to-market engine. Reporting to the Chief Revenue Officer and serving as their second in command across the GTM organization, as well as a strategic partner to the VP, Data. This leader owns the operational backbone that connects Sales, Marketing, Customer Success, and Customer Experience into one aligned, high-performing revenue team.

This is a role for a strategic operator: someone who can shape GTM strategy alongside the CRO, represent revenue operations at the leadership table, and translate ambitious growth goals into the systems, processes, and insights that make them achievable. You will drive operational efficiency, pipeline integrity, forecasting accuracy, and consistent execution against business goals; and you'll act on behalf of the CRO to keep the entire GTM org moving in the same direction.

Your work will span six core areas of ownership:

WHAT YOU’LL DO

1. GTM Leadership & Strategic Partnership to the CRO

• Serve as the CRO's second in command across the Sales-Assisted GTM organization — a trusted proxy in leadership forums, cross-functional decisions, and day-to-day operational leadership
• Partner with the CRO to shape GTM strategy, annual planning, and resource allocation across Sales, Marketing, Customer Success, and Customer Experience
• Facilitate alignment among GTM leaders on strategic questions such as ICP targeting, lead qualification criteria, joint planning, and SLAs
• Represent the revenue organization in executive level reporting, and drive accountability against company growth goals

2. Revenue Tech Stack Ownership & Evolution

• Own the strategy, architecture, and optimization of the full revenue operations and website tech stack, including CRM, marketing automation, CS platforms, and reporting tools (HubSpot,Avoma, Hightouch and lead router).
• Set the multi-year roadmap for the GTM systems landscape; evaluate, implement, and sunset tools to support growth and scale
• Audit system health, integrations, and utilization; drive adoption through enablement and training across teams

3. Data Integrity & Systems Governance

• Partner with Data team to own a shared governance model — clean, connected revenue data with consistent definitions across systems
• Set CRM, opportunity management, and data hygiene standards that scale with the business
• Co-own the workflows that deliver insights, recommendations, and next steps to GTM teams as part of the RevOps / Customer Insights / Data Engineering pod — jointly deciding definitions, priorities, and what ships

4. Forecasting, Reporting & Revenue Analytics

• Contribute to and serve as a stakeholder in the company's revenue forecasting, pipeline analysis, and performance reporting, supporting accurate planning across the revenue organization
• Build and maintain the core suite of RevOps dashboards spanning funnel metrics and key SaaS indicators (ARR, CAC, CLTV, NRR), ensuring consistency between Hubspot and the data warehouse
• Lead recurring insight forums such as a monthly Revenue Metrics Review, surfacing trends and driving strategic decisions with data

5. Lead Lifecycle, Funnel & Process Optimization

• Own the full lead-to-renewal lifecycle, including routing, qualification, handoffs, funnel metrics, and attribution modeling
• Partner with Marketing on lead scoring, campaign effectiveness, and continuous CRO of the website
• Map, refine, and document core revenue workflows (e.g., lead management, sales-to-CS handoff) to drive clarity, consistency, and efficiency at scale

6. Strategic Initiatives & Revenue Growth Programs

• Lead high-impact, cross-functional initiatives that enhance revenue performance — system upgrades, process transformations, and org-wide alignment programs
• Develop business cases and secure executive buy-in for longer-term investments in the GTM engine
• Collaborate with Customer Success and Data team on churn analysis, health scores, and upsell/cross-sell insights that lead to repeatable processes to expand revenue from the existing base

WHAT YOU BRING

• 8+ years of experience in Revenue Operations ideally as a one person team, Sales or Marketing Operations
• A minimum of 1 year in a leadership revenue operations role aligning sales, marketing and customer success teams in a 100+ person company that is scaling revenue up to 50M.
• A strong cross-functional leader operating as a strategic partner to executive GTM leadership, with the judgment and credibility to act on a CRO's behalf
• Strong experience managing and optimizing CRM and revenue systems and tools (HubSpot, Segment, Amplitude, Looker, etc.)
• Deep understanding of sales funnels, customer journeys, and SaaS metrics (ARR, CAC, CLTV, NRR, etc.)
• AI Fluency: You stay curious about AI, test tools that are relevant to your work, and apply them thoughtfully - not just for efficiency, but to expand your scope and impact.
• Strong analytical skills and comfort building executive-level reporting and dashboards across multiple tools
• Proven ability to lead through influence, align senior stakeholders, and drive change across a cross-functional organization
• Excellent communication and project management skills, with experience presenting to executive audiences
• Self-starter who thrives in a fast-paced, remote-first environment

WHY JOIN SORTLY

• Opportunity to work with a passionate and dedicated team
• A culture that fosters innovation, growth, and collaboration
• Competitive salary and benefits package
• Chance to make a significant impact on the future of inventory management
• Annual off-site retreats
• Home office stipend
• 401k match
• Yearly learning and development reimbursement

Annual Salary: $175,000 - $184,000

The salary band outlined above reflects compensation levels that are competitively benchmarked based on geographic location. Where an individual may fall within this band is determined by market data specific to their location, ensuring fairness and alignment with our compensation philosophy.