Rowan Trollope, born on July 1, 1971, has made a mark in the technology sector as a seasoned CEO and board member. Before taking the reins at Smartsheet, he served as CEO of Five9, an intelligent cloud software company, demonstrating...

Rowan Trollope, born on July 1, 1971, has made a mark in the technology sector as a seasoned CEO and board member. Before taking the reins at Smartsheet, he served as CEO of Five9, an intelligent cloud software company, demonstrating his leadership in software innovation. His background includes crucial roles at Cisco Systems, where he led the Applications Group and Collaboration Technology Group. This kind of experience has given him deep insights into building effective technology solutions. His tenure at Smartsheet saw him direct the company through critical phases until his resignation in late 2022, without any disputes regarding the company's operations. Notably, during his leadership, he was recognized for his focus on performance metrics tied closely to company goals. In 2022, his compensation was reported at $469,754, structured primarily around his salary without stock grants or bonuses that year. He has also been active in the boardroom, joining Smartsheet’s Board in 2020, reflecting his commitment to shaping company strategy. Rowan Trollope exemplified the role of a modern tech executive with an emphasis on data-driven decision-making and strategic foresight.

Quick Links

1. Rivals

2. Holdings

3. Insider Trading

4. Compensation History

5. Other Five9 CEOs

F

Rowan Trollope

CEO of Five9

Education

Not specified

Field of Expertise

Technology & Engineering - Technology

Sector of Economy

Technology

Born

January 1, 1971 - 54 years ago

CEO of Five9 for

6 years 11 months (May 2018 - Present)

Previous Experience

Senior Vice President and General Manager at Cisco Systems, Inc.

Rivals

Competitors/colleagues of Rowan Trollope

Z

Eric Yuan

Founder and CEO of Zoom Video Communications, Inc.

2023 Compensation

Stock

$995.19K

Salary

$10.00K

Bonus

$721.00

Other

$1.83M

Total Holdings

$1.64B

Z

Greg Tomb

CEO of Zoom Video Communications, Inc.

2023 Compensation

Stock

$0.00

Salary

$10.00K

Bonus

$721.00

Other

$1.83M

Total Holdings

$35.33M

Holdings

See how much did Rowan Trollope make over time.

Rowan Trollope has been active in insider trading, particularly between 2021 and 2024. His trades reflect a healthy engagement with his holdings, with notable values: $388.61K in September 2021, dropping to $261.78K by October 2022. This pattern shows intentionality and...

Rowan Trollope has been active in insider trading, particularly between 2021 and 2024. His trades reflect a healthy engagement with his holdings, with notable values: $388.61K in September 2021, dropping to $261.78K by October 2022. This pattern shows intentionality and a strategic approach to managing wealth. By June 2024, his transactions peaked at about $1.01M, indicating strong performance within his investment strategies. His trading history involved consistent monthly transactions averaging upwards of $300K, suggesting a robust financial position tied closely to the performance of his companies. As he transitioned out of his CEO role at Smartsheet, he remained vested in the business’s growth, hinting at a long-term view on investments instead of merely capital gain.

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Total Stock Sold

$49.84M

FIVN

$49.84M

506,061 FIVN shares

What if they kept their stock?

If Rowan Trollope didn't sell their stock, today they would have:
Extra FIVN506,061 shares worth $38.86M.
This is -22.04% and $10.99M less than what they got when they sold the stock.

Charitable Transactions

FIVN

70,702 shares

FIVN

Recent Charitable Transactions

FIVN

39,700 shares

FIVN

Apr 5, 2022

Charity

FIVN

31,002 shares

FIVN

Dec 6, 2021

Charity

Insider Trading

See recent insider trades of Rowan Trollope.

FIVN

$557.90K

FIVN at $90.23/share

Sep 6, 2022

Sale

FIVN

$709.73K

FIVN at $120.11/share

Aug 11, 2022

Sale

FIVN

$570.82K

FIVN at $116.49/share

Aug 5, 2022

Sale

FIVN

$200.19K

FIVN at $100.10/share

Jul 6, 2022

Sale

FIVN

$824.54K

FIVN at $100.64/share

Jun 6, 2022

Sale

FIVN

$219.29K

FIVN at $109.65/share

May 5, 2022

Sale

FIVN

39,700 shares

FIVN

Apr 5, 2022

Charity

FIVN

39,700 shares

FIVN

Apr 5, 2022

Charity

FIVN

$232.79K

FIVN at $116.40/share

Apr 5, 2022

Sale

FIVN

$489.72K

FIVN at $99.44/share

Mar 4, 2022

Sale

Compensation History

See how much did Rowan Trollope make over time.

In terms of compensation, Rowan Trollope received a total of $469,754 in 2022. Of this amount, $461,635 was from salary, and he also received $8,119 from the company’s 401(k) matching contributions. There were no bonuses or stock grants vested during this period, suggesting the focus remained on performance metrics that fell short of expectations. This arrangement was actually quite typical, as the company tied most incentives to long-term performance metrics rather than immediate returns. His earlier compensation packages highlighted a mix of salary and performance bonuses, like his target bonus for the fiscal year 2019, which was set at a significant $661,250. This reflects his role's demands and accountability towards shareholder interests while emphasizing long-term goals over immediate pay.

Year

2022

Total Compensation

$469.75K

Salary

$461.64K

Board Justification

The compensation philosophy is designed to attract and retain exceptional executive officers, ensuring alignment with long-term shareholder interests and accountability for key business objectives.

Bonus

$0.00

Board Justification

The annual incentive bonus for the fiscal year ended January 31, 2023 was awarded in cash rather than equity, with a payout at 77% of target due to performance metrics not being fully met.

Other

$8.12K

Board Justification

This amount represents the 401(k) plan matching contributions made by the Company for Rowan Trollope.

Restricted Stock

$0.00(0 RSU)

Board Justification

No stock awards vested in 2022 as the RSUs and PSUs are subject to performance metrics and vesting schedules that extend beyond the fiscal year.

Performance Metrics

The performance metrics for the annual incentive bonus included calculated billings and cash operating expense, with a DEI Bonus Factor adjustment.

Other Five9 CEOs

Here are other CEOs of Five9

Michael Burkland

Ex-CEO of Five9

January 2008 - December 2017