ContractsCounsel Logo

Stock Option Cliff

Clients Rate Lawyers on our Platform 4.9/5 Stars
based on 7,612 reviews
Home Blog Stock Option Cliff

Jump to Section

Need help with an Option Grant?

CREATE A FREE PROJECT POSTING
Post Project Now

A stock option cliff refers to a specific period within vesting schedules during which no stock options become vested and employees don't gain ownership rights. Once the cliff period expires, the remaining stock options vest according to a predetermined schedule, such as monthly or annually. Let us delve deeper to learn more about the stock option cliff and its relevant aspects below.

Key Purposes of a Stock Option Cliff

Here's how the stock option cliff works:

  • Vesting Period: Stock options are typically subject to a vesting period, during which the employee must remain employed with the company to earn the right to exercise the options.
  • Cliff Milestone: There is a cliff milestone at the end of the vesting period. This represents a specific point in time, often the first anniversary of the grant date, where a portion or all of the stock options become exercisable. It acts as a retention trigger, motivating employees to stay with the company until the cliff milestone is reached.
  • Gradual Vesting: After the cliff milestone, the remaining stock options typically vest gradually over time. This encourages continued employment and incentivizes employees to remain committed to the company beyond the initial cliff. For instance, options may vest monthly or quarterly over the remaining vesting period until the options are fully vested.

Benefits of Implementing a Stock Option Cliff

Implementing a stock option cliff can provide several benefits to companies. Here are some of the key advantages associated with the same:

  • Enhanced Employee Retention: By incorporating a stock option cliff, companies can improve their ability to retain talented and high-performing employees. The cliff acts as a retention mechanism by incentivizing employees to stay with the company for a specific period, thereby reducing turnover and retaining valuable talent.
  • Increased Employee Loyalty and Engagement: Stock options with a cliff help align the interests of employees with the long-term success of the company. Employees are likely to feel a sense of loyalty and dedication to achieving the organization's goals when they have a vested interest in the company's performance. This increased engagement can lead to improved productivity and commitment from employees.
  • Alignment with Company Goals: The stock option cliff ensures that employees are vested in the company's long-term performance. As the stock options become valuable only if the stock price increases over time, employees are motivated to contribute to the company's growth and success. This alignment of interests can foster stronger teamwork and a shared commitment to achieving strategic objectives.
  • Mitigation of Short-Term Thinking: Incentivizing employees to remain with the company for a specific duration through a stock option cliff helps counteract short-term thinking. Instead of seeking quick gains and potentially leaving for other opportunities, employees are encouraged to focus on the long-term success of the organization. This can lead to more sustainable decision-making and strategic planning.
  • Competitive Advantage in Talent Acquisition: The presence of a stock option cliff can make a company more attractive to potential hires. Candidates who value the opportunity to gain ownership in the company and benefit from its future success may be more inclined to join an organization with a robust stock option program. This can provide a competitive edge in attracting top talent, particularly in industries where competition for skilled employees is fierce.
  • Stability and Continuity: Implementing a stock option cliff can contribute to a more stable and committed workforce. When employees are motivated to stay with the company over the long term, it reduces the disruptions caused by frequent turnover. This stability enables smoother operations, continuity in project execution, and the accumulation of institutional knowledge within the organization.
Meet some lawyers on our platform

Janice K.

1 project on CC
View Profile

Ryenne S.

439 projects on CC
View Profile

Antonella C.

1 project on CC
View Profile

Scott S.

41 projects on CC
View Profile

Drawbacks of Implementing a Stock Option Cliff

While implementing a stock option cliff can provide benefits, it's important to consider potential drawbacks as well. Here are some of the possible disadvantages associated with it:

  • Limited Liquidity: Stock options may lack liquidity, meaning employees cannot easily convert them into cash. This can be a drawback for employees who are seeking immediate financial rewards or facing personal financial needs. The lack of liquidity may diminish the perceived value of stock options, especially if employees are uncertain about the future performance of the company.
  • Retention of Unmotivated Employees: The stock option cliff may inadvertently retain employees who are not truly motivated or committed to the company's success. Some individuals may stay solely to reach the cliff milestone and cash in on their options, rather than being driven by a genuine interest in the company's growth. This can lead to a less engaged and productive workforce in the long run.
  • Market Volatility: The value of stock options is directly influenced by the stock price, which can be subject to substantial fluctuations in the market. Employees may feel discouraged or frustrated if the stock price decreases or remains stagnant, potentially diminishing their motivation and loyalty. This volatility can undermine the effectiveness of the stock option cliff as a retention tool.
  • Administrative Complexity: Implementing and managing stock option programs can be administratively complex and time-consuming. Companies need to ensure accurate record-keeping, track vesting schedules, and communicate the details of the program to employees effectively. Failure to effectively administer the stock option cliff can lead to confusion, dissatisfaction, and legal complications.
  • Potential Inequities: Stock option cliffs may unintentionally create inequities among employees. For example, if new employees are subject to longer cliffs than existing employees, it can create a sense of unfairness and dissatisfaction. Additionally, too long cliffs may disproportionately benefit senior employees, potentially discouraging the retention of junior talent.
  • Diminished Flexibility: Stock option cliffs restrict employees' ability to exercise their options until the specified cliff milestone is reached. This lack of flexibility can be limiting for employees who may need or desire to exercise their options earlier for personal financial reasons. It can also make it challenging for employees to take advantage of other opportunities that may arise before the cliff is reached.

Key Terms for the Stock Option Cliff

  • Exercisability: The state in which stock options can be exercised and converted into shares of stock, allowing employees to become owners of the company.
  • Grant Date: The date on which stock options are initially awarded or granted to an employee, establishing the terms and conditions of the option grant.
  • Forfeiture: The loss of unvested stock options by an employee who leaves the company before reaching the cliff milestone or completing the full vesting period.
  • Incentive Stock Options (ISOs): Stock options that meet specific criteria outlined by tax regulations, providing certain tax advantages to employees upon exercise and sale of the stock.
  • Non-Qualified Stock Options (NSOs): Stock options that do not meet the criteria set for ISOs, subjecting employees to ordinary income tax upon exercise based on the difference between the exercise price and the fair market value of the stock.

Final Thoughts on the Stock Option Cliff

Stock option cliffs serve as a valuable tool for companies to retain key talent, align employee interests with long-term company goals, and promote stability within the workforce. By implementing a stock option cliff, companies can incentivize employees to remain with the organization, fostering loyalty, engagement, and a shared commitment to the company's success. However, it is essential to design and administer stock option programs carefully, considering factors such as liquidity, market volatility, and potential inequities while also incorporating additional retention strategies to create a comprehensive and effective employee incentive program.

If you want free pricing proposals from vetted lawyers that are 60% less than typical law firms, click here to get started. By comparing multiple proposals for free, you can save the time and stress of finding a quality lawyer for your business needs.

How ContractsCounsel Works
Hiring a lawyer on ContractsCounsel is easy, transparent and affordable.
1. Post a Free Project
Complete our 4-step process to provide info on what you need done.
2. Get Bids to Review
Receive flat-fee bids from lawyers in our marketplace to compare.
3. Start Your Project
Securely pay to start working with the lawyer you select.

Meet some of our Lawyers

Scott S. on ContractsCounsel
View Scott
5.0 (16)
Member Since:
July 28, 2020

Scott S.

Principal
Free Consultation
New York, NY
42 Yrs Experience
Licensed in NY
New York University School of Law

I have over 25 years' experience representing individual and company clients, large and small, in transactions such as mergers and acquisitions, private offerings of securities, commercial loans and commercial endeavors (supply contracts, manufacturing agreements, joint ventures, intellectual property licenses, etc.). My particular specialty is in complex and novel drafting.

Brianna N. on ContractsCounsel
View Brianna
5.0 (2)
Member Since:
June 16, 2021

Brianna N.

Attorney
Free Consultation
New York
7 Yrs Experience
Licensed in NY
Touro Law School

Brianna is a well-respected New York licensed attorney with a Juris Doctorate degree in law from Touro College Jacob D. Fuchsberg Law School and bachelor’s degree in Business Administration and Management from Dowling College. Since becoming an attorney, she has practiced in various areas including business law, corporate law, residential real estate, commercial real estate, criminal law, traffic law, employment law, landlord tenant law, estate planning, and has represented intermediaries in procurement and the personal protective equipment industry. Brianna has broad and extensive business experience; She is an entrepreneur and co-owner of a microtechnology manufacturing company that was built by her and her partner, where she also served as the Chief Legal Officer and Human Resource Manager for the company. While building the manufacturing business, she created a brokerage firm for business transactions and has managed several other businesses which she has ownership interest in. Brianna’s involvement in these various businesses over the past 15 years provides a unique skillset to her clients; Not only does she understand contractual principals and obligations from a legal perspective while drafting and negotiating agreements, but she also has the foresight, experience, and ability to ensure the agreement reflects the practical aspects of the business. Based on the client’s needs and desired outcome, she has the forethought to cover different angles that would be overlooked from a legal standpoint, and as a result she is able to help prevent unforeseen business ramifications. She conducts extensive risk assessments on behalf of her clients and minimizes exposure to potential liability without “over lawyering” agreements. One of Brianna’s main areas of focus is drafting and negotiating agreements. Negotiation is a passion of hers which was applied in law school while she was a member of the Alternative Dispute Resolution Society, notably winning Touro Law School’s intraschool negotiation competition. In her more recent years, Brianna has removed herself from her various business interests to focus on her law practice. Brianna has a strong moral compass and believes in quality over quantity. She treats every client as a top priority; thus, she will not take on many cases at a time because she wants to give each client the focus and attention they deserve. She has sharp attention to detail and is a forceful advocate for every client. Brianna has broad and extensive business experience; She is an entrepreneur and co-owner of a microtechnology manufacturing company that was built by her and her partner, where she also served as the Chief Legal Officer and Human Resource Manager for the company. While building the manufacturing business, she created a brokerage firm for business transactions and has managed several other businesses which she has ownership interest in. Brianna’s involvement in these various businesses over the past 15 years provides a unique skillset to her clients; Not only does she understand contractual principals and obligations from a legal perspective while drafting and negotiating agreements, but she also has the foresight, experience, and ability to ensure the agreement reflects the practical aspects of the business. Based on the client’s needs and desired outcome, she has the forethought to cover different angles that would be overlooked from a legal standpoint, and as a result she is able to help prevent unforeseen business ramifications. She conducts extensive risk assessments on behalf of her clients and minimizes exposure to potential liability without “over lawyering” agreements. Additionally, she specializes in drafting and negotiating agreements. Negotiation is a passion of hers which was applied in law school while she was a member of the Alternative Dispute Resolution Society, notably winning Touro Law School’s intraschool negotiation competition. In her more recent years, Brianna has removed herself from her various business interests to focus on her law practice. Brianna has a strong moral compass and believes in quality over quantity. She treats every client as a top priority; thus, she will not take on many cases at a time because she wants to give each client the focus and attention they deserve. She has sharp attention to detail and is a forceful advocate for every client.

Jeff C. on ContractsCounsel
View Jeff
4.9 (4)
Member Since:
July 31, 2020

Jeff C.

Outside General Counsel / Business Attorney
Free Consultation
Colorado
36 Yrs Experience
Licensed in CO, OR
University of Oregon

Experienced and broad based corporate/business attorney and Outside General Counsel (OGC), for start-ups, small businesses and growing companies of all sizes, advising and assisting clients with corporate and LLC formation, contracts and agreements, internet and terms of use/service agreements, trademarks and intellectual property protection, the purchase and sale of businesses (M&A), labor and employment matters, compliance and risk management, corporate governance, and commercial leasing matters. See other reviews on my website at www.ogcservices.net/reviews

Cynthia F. on ContractsCounsel
View Cynthia
Member Since:
July 24, 2020

Cynthia F.

Managing Partner
Free Consultation
Los Angeles, CA
13 Yrs Experience
Licensed in CA
Western State - College of Law

I run a small law firm in Pasadena, CA. I have been practicing for almost 10 years and the other attorneys at my firm each have 12+ years of experience. We focus on business and employment law, protecting and defending business owners. While my clients are all sizes, I particularly enjoy helping smaller companies and individuals manage their legal needs without the high price tag.

Jessica K. on ContractsCounsel
View Jessica
Member Since:
January 16, 2021

Jessica K.

Litigation Attorney
Free Consultation
Florida
7 Yrs Experience
Licensed in FL
University of Florida Levin College of Law

I assist individuals and businesses across the state of Florida with litigation, contract drafting, contract interpretation, and issues that may arise because of contract terms, including demands (cease-and-desist letters) and litigation. I have experience with non-compete agreements, privacy policies, website terms, settlement agreements, intellectual property disputes, and many other disputes. Please reach out if I can help you with a litigation- or contract-related project!

Stephen F. on ContractsCounsel
View Stephen
Member Since:
July 29, 2020

Stephen F.

Attorney
Free Consultation
Chicago
14 Yrs Experience
Licensed in IL
Western Michigan

Stephen began practicing law in 2009 working as an associate documenting construction loans for local banks. Since the beginning of his career Stephen has expanded his practice to serve individuals and companies by performing commercial and residential real estate transactions, aiding in business organization and general corporate matters. While representing businesses Stephen has supports his clients by providing counsel on leasing, business succession, stock purchase agreements, mergers and acquisitions, constructions loans, as well as contract litigation. Stephen works to ensure that all matters are handled in a timely manner and to keep open communication with his clients.

Christopher J. on ContractsCounsel
View Christopher
Member Since:
August 4, 2020

Christopher J.

Attorney and Counselor at Law
Free Consultation
Ann Arbor, MI
24 Yrs Experience
Licensed in MI
Detroit College of Law at Michigan State University

Experienced attorney focusing on estate planning, probate administration, business formation and counseling, and consumer bankruptcy.

Find the best lawyer for your project

Browse Lawyers Now
CONTRACT LAWYERS BY CITY
STOCK OPTION CLIFF LAWYERS BY CITY
Learn About Contracts
See More Contracts
other helpful articles

Quick, user friendly and one of the better ways I've come across to get ahold of lawyers willing to take new clients.

View Trustpilot Review

Contracts Counsel was incredibly helpful and easy to use. I submitted a project for a lawyer's help within a day I had received over 6 proposals from qualified lawyers. I submitted a bid that works best for my business and we went forward with the project.

View Trustpilot Review

I never knew how difficult it was to obtain representation or a lawyer, and ContractsCounsel was EXACTLY the type of service I was hoping for when I was in a pinch. Working with their service was efficient, effective and made me feel in control. Thank you so much and should I ever need attorney services down the road, I'll certainly be a repeat customer.

View Trustpilot Review

I got 5 bids within 24h of posting my project. I choose the person who provided the most detailed and relevant intro letter, highlighting their experience relevant to my project. I am very satisfied with the outcome and quality of the two agreements that were produced, they actually far exceed my expectations.

View Trustpilot Review

How It Works

Post Your Project

Get Free Bids to Compare

Hire Your Lawyer

GET BIDS NOW

Want to speak to someone?

Get in touch below and we will schedule a time to connect!

Request a call

Find lawyers and attorneys by city