Chief of Staff to the Head of Sales

About the role

This position is designed to support Assured's sales leadership by serving as a strategic partner and operational facilitator for the go-to-market team. You will work closely with the Head of Sales to coordinate initiatives, manage operational rhythms, and assist in executing deals that contribute to revenue growth. The role requires a proactive and organized individual capable of balancing strategic planning with tactical execution in a fast-paced environment. You will be instrumental in ensuring that the sales organization operates smoothly, aligns with company goals, and achieves its targets. This position offers an exciting opportunity to influence the sales strategy and contribute directly to the company's growth trajectory.

Key facts

What you'll do

• Act as a trusted advisor and proxy for the Head of Sales, managing their strategic priorities and preparing them for critical internal and external engagements.
• Design, implement, and oversee the sales team's operational cadence, including pipeline reviews, forecast discussions, quarterly business reviews, and other regular meetings to ensure alignment and accountability.
• Develop, maintain, and improve reporting dashboards and analytics tools to provide clear visibility into pipeline health, forecast accuracy, and overall team performance metrics.
• Create and update sales enablement materials such as presentations, one-pagers, case studies, and other collateral to support customer meetings and internal training.
• Facilitate collaboration and alignment between Sales and other departments like Marketing, Customer Engineering, Product, and Finance to ensure cohesive execution of strategies and initiatives.
• Analyze complex business challenges such as market segmentation, customer targeting, and pricing strategies, providing data-driven recommendations to inform decision-making.
• Support the hiring process by assisting with candidate evaluation, interview scheduling, and onboarding new sales team members to ensure smooth integration.
• Prepare strategic memos, executive summaries, and communication materials for leadership to inform decision-making and strategic planning.
• Coordinate cross-functional projects and initiatives to ensure timely delivery and alignment with sales objectives.
• Monitor industry trends, competitive landscape, and emerging technologies to inform sales strategies and identify new opportunities.
• Assist in developing and refining sales strategies, operational processes, and best practices to improve efficiency and revenue growth.
• Track progress against strategic objectives, key performance indicators (KPIs), and operational goals, providing regular updates to leadership.
• Support the sales leadership in preparing for investor meetings, board presentations, and other high-level engagements.
• Help streamline internal processes and workflows to improve productivity and reduce bottlenecks within the sales organization.
• Manage special projects related to sales enablement, process improvements, or strategic initiatives as assigned by the Head of Sales.
• Foster a culture of continuous improvement, data-driven decision making, and collaboration within the sales team and across departments.

Requirements

• 5 to 7 years of professional experience, including 2 to 4 years in management consulting at a top firm such as Bain, McKinsey, or BCG, or in a sales strategy, revenue operations, or chief of staff role at a fast-growing company.
• Proven track record of working in high-growth environments and supporting senior leadership in strategic initiatives.
• Excellent written and verbal communication skills, with the ability to distill complex information into clear, concise messages for diverse audiences.
• Strong analytical skills, including experience building financial models, strategic frameworks, and interpreting data to inform decisions.
• Demonstrated ability to work independently, prioritize multiple tasks, and drive results in a dynamic environment.
• High level of personal accountability, with a proactive approach to problem-solving and task completion.
• Collaborative mindset and ability to influence cross-functional teams without direct authority.
• Experience managing multiple projects simultaneously while maintaining attention to detail and meeting deadlines.
• Familiarity with sales processes, metrics, and operational best practices.
• Ability to adapt quickly to changing priorities and business needs.
• Comfort working with senior executives and presenting to leadership teams.

Nice to have

• Familiarity with modern sales technology stacks, including CRM platforms, sales engagement tools, and business intelligence software.
• Prior experience working in SaaS or technology companies.
• Knowledge of sales methodologies, pipeline management, and revenue growth strategies.
• Experience with data visualization tools and reporting dashboards.
• Understanding of market segmentation, customer targeting, and pricing strategies.
• Exposure to international markets or working with global teams.

Skills & tools

• Sales Strategy
• Revenue Operations
• Cross-functional Collaboration
• Data Analysis
• Executive Communication
• CRM Platforms
• BI Tools

Practical notes

• Assured offers a competitive compensation package, including a salary range of $180,000-$200,000 and equity options.
• The company provides comprehensive benefits such as a platinum medical, dental, and vision plan, life and disability insurance, and unlimited paid time off.
• Additional benefits include family leave, a 401(k) plan with a 3% company contribution, and work-from-home stipends.
• Health FSAs and HSAs are available to employees.
• Remote team members receive lunch benefits twice weekly and a monthly phone stipend to support their work environment.
• Assured organizes regular team events and offsite gatherings to foster team cohesion and company culture.
• The company is committed to diversity and inclusion and is an equal opportunity employer.
• Candidates should be cautious of recruitment scams; official communication is only conducted via @assured.claims email addresses.
• This role is based on-site at the company's remote working arrangement, supporting the sales leadership directly.