Training and Executive Operations Manager (WFH)
About Penbrothers Penbrothers is an HR & remote talent management partner and one of the fastest growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes. About the Client Our Client is a Dubai-based remote delegation service supporting top MENA founders and VCs by helping them reclaim their time. They specialize in matching busy leaders with tech-savvy, Arabic-speaking, Middle East-based executive assistants—offering highly personalized support that enables clients to focus on high-value, strategic work. In addition to their delegation services, our Client is building a mission-driven digital brand designed to empower people to live with intention and inner freedom. Through science-backed systems, soulful coaching, and holistic support, they help individuals reconnect with themselves and create space for purpose-driven living. As their client base and global presence grow, they’re looking for a sharp and strategic Operations Manager to strengthen internal operations and drive seamless execution across teams. About the Role As Training and Executive Operations Manager , you will be the operational anchor of a high-performing Executive Partner team, ensuring seamless client delivery and exceptional service standards. This role combines strategic leadership with hands-on execution, requiring you to optimize systems, drive performance, and scale operations effectively. Reporting directly to the CEO, you will shape operational strategy, establish processes that enable growth, and lead the team to consistently exceed expectations. This is a high-visibility role with a clear path to Head of Operations, ideal for a results-driven operator ready to influence the company’s next stage of growth. What you’ll do Delivery Oversight & Client Success Own the end-to-end client lifecycle, from onboarding to ongoing relationship management, ensuring consistently exceptional service. Monitor Executive Partner (EP) performance and operational KPIs, proactively identifying gaps and implementing corrective action. Gather and analyze client feedback to anticipate needs, course-correct in real time, and drive continuous improvement. Serve as the voice of the client internally, ensuring alignment between expectations and delivery outcomes. Team Leadership, Training & Coaching Lead, mentor, and inspire a remote team of Executive Partners, driving both performance and engagement. Design and execute comprehensive onboarding programs, equipping new hires to deliver top-tier client support from day one. Shadow and audit EP workflows, providing actionable coaching, performance feedback, and accountability to raise the bar across the team. Manage conflict decisively and maintain a culture of high performance and continuous learning. Operational Systems & Process Optimization Build, refine, and manage internal SOPs, playbooks, and workflows that scale operations efficiently. Partner cross-functionally with Training, Partnerships, and the CEO to streamline processes and strengthen operational alignment. Maintain dashboards, reporting tools, and automation (Notion, Slack, Google Workspace, Zapier) to drive visibility, accountability, and data-informed decisions. Identify operational bottlenecks and implement solutions to increase speed, quality, and client satisfaction. Escalation Management & Strategic Problem Solving Act as the primary escalation point for client or operational issues, resolving challenges swiftly and professionally. Anticipate risks, manage expectations proactively, and safeguard client trust and operational integrity. Embed a culture of prevention over reaction, elevating the team’s maturity and resilience under pressure. Requirements What You Bring Has 4+ years of experience in EA, Operations Manager, or Chief of Staff-type roles. Brings 1-2 years of experience mentoring or managing professionals in a team leadership capacity. Possesses proven stakeholder or client-facing communication experience. Is tech-fluent, comfortable with tools such as Google Workspace, Notion, Slack, Zapier, Hubspot, and Outlook. Demonstrates a work style characterized by high autonomy, being self-managed, and outcome-driven. Can align with MENA hours and is flexible for urgent needs. Communicates fluently, assertive, and proactive in English, both written and spoken. Is experienced in async, remote team environments. Thrives in change, chaos, and shifting priorities, showcasing operational agility. Excels in day-to-day oversight, tracking EP tasks, providing nudges when needed, and ensuring delivery. Knows how to level up underperformers through performance coaching. Is assertive across stakeholders and prioritizes an async-first approach to communication. Understands executive expectations and high standards, demonstrating client maturity. Builds systems rather than just putting out fires, indicating strategic operations thinking. Is proficient with tools like Notion, Slack, Trello, and Google Workspace. Has cross-timezone fluency and a strong documentation culture, essential for remote teaming. Nice-to-Haves EA Coaching: Experience in EA coaching will be valuable as you'll mentor and support a growing Executive Partner (EP) team. Onboarding & Training: Skills in onboarding and training contribute to faster EP ramp-up and delivery. Process Improvement: Ability to drive process improvement supports scale and system building. Conflict Resolution: Experience in conflict resolution helps manage client escalations diplomatically. Agency/BPO Background: Familiarity with high-accountability delivery models from an agency or BPO background is beneficial. Bonus: You've worked as a tech-savvy EA and know what great service feels like Hiring Process We utilize AI tools to enhance our hiring efficiency and ensure a fair evaluation of all candidates. As a result, candidates who passed our initial evaluations should expect an AI Interviewer as a component of our recruitment process. This is supervised by Human Talent Acquisition Experts who will also engage with you throughout your application journey. What You’ll Get At Penbrothers , we are obsessed with creating positive employee experiences. Here you’ll find an environment that nurtures learning and provides opportunities for growth. You’ll have the opportunity to make an impact on fast-growing startups and dynamic companies. Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience. Employee as our biggest asset: We are genuinely invested in our people’s career and welfare. Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home. Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth. Originally posted on Himalayas