Head of Executive Operations (Chief of Staff)

JiffyShirts is seeking a dynamic and proactive leader as the Head of Executive Operations (otherwise known as Chief of Staff). The Head of Executive Operations role is designed to serve as an extension of and right hand to the President (Peter Gerstberger, former Chief Digital & Strategy Officer at The Honest Company, ex-Amazon and ex-Ring leadership) and a facilitator of effectiveness for the executive team, including the CEO. The role will have around-the-clock exposure to the company’s daily operational functions, ensuring strategic objectives are met while streamlining processes and optimizing productivity. The Head of Executive Operations will travel globally with the President and CEO while following a demanding and intensive schedule that spans a large number of time zones.  This allows the Head of Executive Operations to be exposed to the priorities, communications, strategic thought process, decision making, management and leadership of the President and CEO. The Head of Executive Operations executes across multiple cross-functional strategic initiatives across the company. The ideal candidate will possess a combination of strategic thinking, executive presence, organizational prowess as well as process optimization, project management and communication skills, along with a keen ability to adapt to the President’s style and vision. The Head of Executive Operations will have a dedicated 18 month growth plan to become a future leader with P&L responsibility within the company.

Candidates must live in ET or CT timezone

Key Responsibilities:

• Work closely with the President and CEO to understand their objectives, priorities, strategic thought process, communication style, and decision-making process
• Maximize the President and CEO’s potential by taking ownership of lower priority tasks to free up the President and CEO's time for higher-value activities
• Collaborate with cross-functional teams to ensure effective execution of company-wide strategic initiatives and projects
• Develop a deep understanding of the company's operations, culture, and goals to provide valuable insights and recommendations to sustain the company’s track record of growth and innovation
• Continuously refine and optimize processes and project management discipline to enhance organizational efficiency and effectiveness
• Assemble and analyze financial and operational data to support strategic decision-making and identify areas for improvement

Preferred Qualifications:

• Bachelor's degree in business, management, or related field; MBA preferred from a top-tier program
• 2-3 years of experience in a top-tier management consulting firm or VC environment (e.g., Bain, BCG, McKinsey)
• 2-3 years of experience in DTC e-commerce company highly preferred
• Strong written and verbal communication skills, along with the ability to adapt communication style to various stakeholders
• Understands how to run a business from end to end
• High level of emotional intelligence and ability to build positive relationships with colleagues at all levels; strong gravitas and capable of gaining respect from the Executive Team
• Excellent Powerpoint/presentation skills with experience presenting to senior executive levels in organizations
• Exceptional organizational and multitasking skills, with a demonstrated ability to handle complex projects and tasks simultaneously
• Proven success in special projects, project management and financial modeling
• Detail-oriented and process-driven mindset, with a focus on optimizing workflows and improving efficiency
• Ability and eagerness to operate on an intensive schedule while traveling globally (15%)
• Demonstrated ability to work independently, take initiative, and make informed decisions

Why you’ll love working here:

• Direct mentorship and exposure to Peter Gerstberger, Jiffy.com President, former Chief Digital & Strategy Officer at The Honest Company, former leader at Amazon and Ring; Chris Serflek, Jiffy.com CEO, Visionary multiple Founder with 20 years of experience running profitable ecommerce companies
• Equity in a hyper growth, founder-owned, fully bootstrapped company with 9 figure topline, 8 figure EBITDA
• Flexibility to work remotely with a high-performing, A-player team
• High visibility and influence in shaping cutting edge e-commerce solutions
• Opportunity to lead product innovation in the rapidly evolving AI and image processing space
• Collaborative and high growth environment, with direct impact on the company’s strategic direction
• 18 month growth plan and exit opportunity to become a P&L leader within the company