How to build a long-term relationship with a virtual executive assistant

There is no guarantee that any team member will stick around for as long as you need them to.  but if you want to build a long-term relationship with a virtual executive assistant, we’ve discovered three key elements make a difference when it comes to EA retention: culture and wellness, learning and growth, and compensation and benefits.

In this post, we’ll share actionable strategies we use to provide EAs with an unparalleled career experience, and explain how you can apply these insights to build a productive, long-term relationship with your own EA.

Table of contents

1. Culture and Wellness
2. Learning and Growth
3. Compensation and Benefits

Building a lasting relationship with a virtual executive assistant isn’t just about avoiding the hassle of hiring someone new; it’s about protecting your own productivity. Every time you lose an EA, you face not only the direct costs of recruiting and onboarding a new team member, but also a disruption in productivity among executives who were supported by the EA.

This challenge can feel even more daunting for startup leaders working with contractor EAs. Maintaining long-term loyalty may seem beyond your control if you don’t have the structure of a traditional employer-employee setup. But at Viva, we know what makes EAs stay and thrive. With over 150 EAs in our network, we’re confident that building strong, lasting partnerships is absolutely possible. The key? Treating your EA like a valued part of your team.

1. Culture and Wellness

One crucial aspect of EA retention is promoting a positive culture and supporting your EA’s well-being. EAs who feel valued, cared for, and connected to their workplace are more likely to stay engaged and committed to their role. At Viva, we’ve found that fostering a sense of belonging and prioritizing well-being creates an environment where EAs can thrive. We achieve this through several initiatives:

• Well-being support: We offer a wellness subsidy, wellness sessions to help EAs maintain their physical and mental health. We empower our EAs to feel energized, focused, and ready to excel in their roles by encouraging healthy habits.
• Community: Being an EA can be demanding, but having a strong network to lean on makes all the difference. At Viva, we’ve cultivated a large, supportive EA community where team members can ask questions, share insights, and exchange resources. This sense of camaraderie helps EAs feel less isolated and better equipped to handle their day-to-day challenges. That’s why we have Thursday trivia, Slack donuts, and Luna Park events.
• Celebrations: Recognizing milestones is key to fostering a positive workplace culture. That’s why we celebrate our EAs in different ways: with welcome meals for new team members, birthday cakes to mark their special day, thoughtful work anniversary treats, and festive end-of-quarter gatherings. These gestures go a long way in making our EAs feel seen, appreciated, and valued.
• Mindfulness initiatives: We regularly offer activities like meditation, yoga, and fun team-building games to offer stress relief. These programs provide a break from the daily grind and allow EAs to unwind while strengthening their connections with their peers.
• Delegation task board: We know that EAs often juggle a high volume of responsibilities. To support their efficiency, we provide a dedicated delegation task board. This allows EAs to pass on lower-priority tasks to other team members or an “assistant’s assistant,” ensuring they can focus on their most impactful work without feeling overwhelmed.
• PTO backfill support: Taking time off is essential for well-being, but no one wants to return to a mountain of work. That’s why we offer PTO backfill support, ensuring executives receive seamless coverage while their EA is away. This thoughtful system helps EAs enjoy their time off without stress, allowing them to maintain balance in their professional lives.

2. Learning and Growth

Another key to retaining EAs is ensuring they feel supported in their professional growth. EAs become more engaged and committed to their roles when they are given the opportunity to expand their skills, develop new competencies, and see a clear path forward in their careers. At Viva, we believe that investing in our EAs’ professional growth is essential, not only for their individual success but also for the long-term success of the executives they support.

• Remote work support: Working remotely requires the right tools and environment to succeed. We provide a generous work-from-home stipend to help EAs create comfortable and productive home workspaces. In addition, we equip EAs with new laptops and offer 24/7 global IT support to ensure they have the technology and assistance they need to perform their best.
• Learning and development opportunities: We actively invest in our EAs’ growth by giving them access to relevant courses, books, and conferences. Whether they want to sharpen their skills or explore new areas of expertise, we encourage ongoing education to help them expand their capabilities and increase their value as executive assistants. We also provide mentorship sessions from leaders across industries: either senior EAs or prominent female executives at some of the biggest startups in the US.
• Customer impact stories: Recognizing the meaningful contributions of EAs is essential for building morale and confidence. We make a point of highlighting moments where our EAs have made a real difference, whether by helping their executive close a major deal, successfully organizing a high-stakes event, or resolving a critical issue. Sharing these success stories reinforces the value EAs bring to their teams and motivates them to continue delivering excellent results.
• Public recognition: Publicly acknowledging EAs in company-wide settings shows their contributions are valued. We regularly give shoutouts during town halls and all-hands meetings to celebrate their hard work and achievements. This kind of recognition not only boosts individual morale but also reinforces the importance of the EA role across the organization.
• Dedicated leader: All our EAs are supported by a dedicated Customer Success Manager. This leader provides ongoing guidance, regular check-ins, and tailored coaching to ensure each EA feels confident, motivated, and empowered to excel in their role. By serving as a trusted mentor, the Customer Success Manager helps EAs navigate challenges, develop their skills, and build lasting relationships with their executives.

3. Compensation and Benefits

• Compensation increases: We conduct regular performance reviews with clear, transparent criteria that outline what it takes to earn a raise once every other quarter. By maintaining this consistency, EAs feel confident that their hard work and growth will be recognized and rewarded.
• Short-term and performance bonuses: We offer bonuses tied to key milestones and achievements, such as EA performance scores from the executive(s) they support.
• Promotions: We provide clear pathways for advancement within our organization. By outlining opportunities for promotion, we give EAs a roadmap for career growth, encouraging them to build long-term careers with us rather than seeking opportunities elsewhere.
• Health and life stability benefits: We offer valuable benefits such as health insurance, paid time off, parental leave, pregnancy accommodations, and return-to-work subsidies (paid childcare for 1 month after returning from parental leave) to provide peace of mind and security. These elements of our EA’s total rewards package demonstrate our commitment to the long-term well-being of our EAs, helping them feel cared for and valued.

If you’re interested in hiring a virtual executive assistant but can’t afford to offer all these perks, book a call with our team: We take care of all the benefits, all you have to do is delegate.