Join us in Miami POSSIBLE 2026
April 27th - 29th
Headed to POSSIBLE? Make it count.
Host your team or clients at a waterfront Sunrise or Sunset Pickleball session at Equalité, hosted by Cover My Leave.
1-hour sessions include instruction, play, paddles, balls, water, and canned cocktails. Up to 8 players. Join solo or as a group.
Spots are limited. Registration required.
MOST COMPANIES HAVE A LEAVE POLICY.
VERY FEW HAVE A LEAVE PLAN.
Cover My Leave specializes in employee leave coverage, pairing teams with seasoned experts (Coverage Partners) for Maternity & Paternity Leaves, Family & Medical Leaves, Short/Long-Term Disability, Bereavement, Sabbaticals, Vacancies (To-Be-Hired), and New Business Ventures.
Areas of Expertise:
Advertising
Marketing
Media
Sales
Communications
Human Resources & Operations
We help leadership teams move faster, navigate complexity, and scale capacity without permanent overhead - as an agile talent partner equally committed to finding the right fit for the role.
Whatever your talent needs are - we’ve got them covered.
We’ve got you covered
Short-term leave
coverage
Turn an employee's absence into an opportunity for momentum. Our experts onboard quickly, work alongside your team, and leave behind a framework that scales.
Maternity, paternity & family medical leaves
Short & long-term disability
Bereavement & sabbaticals
Vacancies (to-be-hired)
Project support
Need a powerhouse team to guide a critical business initiative? Gain expert support for your most important projects.
New business pitches
Rebranding & creative development
Strategic planning (marketing & media)
Organizational restructures & hiring
Expert talent from our global roster, embedded into your team
Our seasoned Coverage Partners act as temporary team members, bringing experience across a variety of sectors, fresh perspectives, and a deep understanding of the industry. They’re senior professionals who understand the importance of strategy and execution, and are in it - not above it.
Teams and Clients benefit from their vast expertise and relationships across categories:
How We Work
1) A Temporary Team Member
We become a part of your team - for as long as you need.
2) Purposeful In-Person
Remote-first by design, you get access to the best talent for your needs across our global network –face-to-face when it matters.
3) Designed to Deliver
A tailored plan that gives you precisely the coverage you need.
“I wanted to acknowledge your outstanding collaboration with our team and say thanks for the proactive engagement...you helped build momentum both in our strategy and results via a relook at our overall approach."
— Carl Loredo, U.S. President, Pizza Hut
“I am pregnant again, and the clients asked if they can have you back for coverage!”
— Senior Account Executive, Amazon Ads
“Jessica is amazing to work with - she’s friendly, professional, and really easy to get along with. She has a great way of achieving goals and building strong relationships. I was always impressed by how effective and driven she is."
— Head of Ad Operations, QT Group, Finland
Meet the Team –
personally involved in every placement
Jessica Ciliento
Principal
20+ years across agencies, brands, and sales. Jessica covered parental leaves for years before founding Cover My Leave – giving her firsthand expertise in seamless transitions and business continuity.
Christina D'Asaro
Principal
20+ years of industry experience across agencies, Fortune 500s, start-ups, and the United Nations – leading global teams in supporting business growth and impact.
“We've done these jobs.
We know what great looks like.”
Jessica Ciliento and Christina D’Asaro each bring 20+ years of experience across agencies, brands, media, and global organizations, and are personally invested in every placement to ensure it’s the right fit.
“As Principals of Cover My Leave, we bring something that's genuinely hard to find: the firsthand experience of having done these jobs ourselves, and the judgment that only comes from years of actually being in the room. We know what great looks like in these roles because we've held them and worked with the industry's best.
That's why we're personally involved in every placement. Because we care deeply about getting it right, for you, for your team, and for the person stepping in. We've both built careers on relationships and trust, and that's exactly how we approach Cover My Leave. When we recommend someone, it's because we truly believe they're the right fit.”
– Jessica and Christina
Have an empty seat to fill?
Leave it to us.
Let our Coverage Partners step in quickly, embrace the role, and maintain momentum – so you can focus on delivering for your clients.
Reach out directly
Jessica Ciliento
Co-Principal, Cover My Leave
(973) 769-4982