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 and fractional support, pairing teams with seasoned experts (Coverage Partners), who provide flexible coverage during: 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
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)
Fractional and project support
Need a powerhouse team to guide a critical business initiative? We deliver outstanding results for your most important projects.
New business pitches
Rebranding & creative development
Strategic planning (marketing & media)
Organizational restructures & hiring
How We Work:
Expert talent embedded in days, not months.
Step 1: Give us 15-minutes
Email your coverage dates, role, and key details. We’ll schedule a brief call to align.
Step 2:
We send a proposal
Scope of work, timeline, and two coverage-level options delivered in 2 business days.
Step 3:
Meet your partner
We match you with the right Coverage Partner and offer option for a 15-min intro call.
Step 4:
Coverage begins
Blueprint, kick-off call, and your partner is embedded, ready to deliver on day one.
Why Cover My Leave?
Our seasoned Coverage Partners bring experience across a variety of sectors, fresh perspectives, and a deep understanding of the industry. They are senior-level professionals who understand the importance of strategy and execution, and are in it - not above it.
Clients benefit from their vast expertise and relationships across categories:
Senior-level talent (15 yrs +)
Coverage Partners with 15+ years across strategy, investment, selling, and brand development. Embedded into your team and ready to deliver on day one.
Access to our entire network
Clients gain access to the full Cover My Leave network. It’s like hiring an entire agency for the cost of a single cover.
Transparent pricing, always
Monthly billing, set in advance. No hour tracking, no reconciliation. Consolidated process.
Meet the Team –
personally involved in every placement
Jessica Ciliento
Co-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
Co-Principal
20+ years across global agencies, Fortune 500s, start-ups, and the United Nations. Christina translates organizational vision into strategic communications that connect and convert.
“We've done these jobs.
We know what great looks like.”
Jessica Ciliento and Christina D’Asaro each bring 20+ years across agencies, brands, media, and global organizations, and are personally invested in every placement to ensure it’s the right fit.
Client Experiences
“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
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