As of September 29, 2026, Five9's top three insider holders are Amit Mathradas (Chief Executive Officer, 716.74K shares), Michael Burkland (Chief Executive Officer, 403.94K shares), Bryan M Lee (Chief Financial Officer, 289.33K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Amit Mathradas | Chief Executive Officer | 716,743 | 0 | 716,743 | 18.5% | 26 Feb, 2026 |
| 2 | Michael Burkland | Chief Executive Officer | 403,945 | 0 | 403,945 | 10.4% | 26 Feb, 2026 |
| 3 | Bryan M Lee | Chief Financial Officer | 289,333 | 0 | 289,333 | 7.5% | 09 Sep, 2026 |
| 4 | Matthew E. Tuckness | Chief Revenue Officer | 281,492 | 0 | 281,492 | 7.2% | 08 Jun, 2026 |
| 5 | Tiffany N. Meriweather | Chief Admin. Legal Officer | 253,249 | 0 | 253,249 | 6.5% | 09 Sep, 2026 |
| 6 | Andy Dignan | President | 237,614 | 0 | 237,614 | 6.1% | 21 Sep, 2026 |
| 7 | Inc. Five9, | President | 233,409 | 0 | 233,409 | 6.0% | 26 Mar, 2025 |
| 8 | Niranjan Vijayaragavan | Chief Technology Officer | 207,734 | 0 | 207,734 | 5.3% | 15 Jul, 2026 |
| 9 | David G Dewalt | Director | 193,201 | 0 | 193,201 | 5.0% | 18 May, 2023 |
| 10 | Rowan M Trollope | Chief Executive Officer | 119,724 | 42,043 | 161,767 | 4.2% | 08 Sep, 2022 |
| 11 | Panos Kozanian | Evp, Product Engineering | 161,671 | 0 | 161,671 | 4.2% | 08 Jun, 2026 |
| 12 | Daniel P. Burkland | Pres. Chief Revenue Officer | 128,926 | 0 | 128,926 | 3.3% | 06 Sep, 2024 |
| 13 | Robert Hornish | Chief Sales Officer | 121,444 | 0 | 121,444 | 3.1% | 15 Jul, 2026 |
| 14 | Barry Zwarenstein | Chief Financial Officer | 92,583 | 0 | 92,583 | 2.4% | 06 Mar, 2025 |
| 15 | Robert Zollars | Director | 76,371 | 0 | 76,371 | 2.0% | 22 May, 2025 |
| 16 | Leena Mansharamani | Svp, Chief Accounting Officer | 51,787 | 0 | 51,787 | 1.3% | 16 Sep, 2026 |
| 17 | Michael J Burdiek | Director | 40,832 | 0 | 40,832 | 1.1% | 22 May, 2026 |
| 18 | Scott Welch | Evp, Telco Services Gm Emea | 30,887 | 0 | 30,887 | 0.8% | 08 Jun, 2022 |
| 19 | David S. Welsh | Director | 29,795 | 0 | 29,795 | 0.8% | 22 May, 2025 |
| 20 | Sue Barsamian | Director | 28,907 | 0 | 28,907 | 0.7% | 22 May, 2026 |
| 21 | Jonathan D Mariner | Director | 27,147 | 0 | 27,147 | 0.7% | 22 May, 2026 |
| 22 | Julie Iskow | Director | 26,117 | 0 | 26,117 | 0.7% | 22 May, 2026 |
| 23 | Sudhakar Ramakrishna | Director | 21,230 | 0 | 21,230 | 0.5% | 30 Sep, 2025 |
| 24 | Maria C Walker | Director | 20,411 | 0 | 20,411 | 0.5% | 22 May, 2026 |
| 25 | Sagar Gupta | Director | 20,349 | 0 | 20,349 | 0.5% | 22 May, 2026 |
| 26 | Kimberly Alexy | Director | 11,117 | 0 | 11,117 | 0.3% | 03 Feb, 2023 |
| 27 | Jack L Acosta | Director | 9,556 | 0 | 9,556 | 0.2% | 16 May, 2024 |
| 28 | Ana G. Pinczuk | Director | 5,632 | 0 | 5,632 | 0.1% | 20 May, 2022 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 17 Sep, 2026 | Andy Dignan | President | Disposed S | 6,986 | $35.00 | $244.51K | 237,614 | Direct |
| 04 Sep, 2026 | Andy Dignan | President | Disposed S | 2,900 | $33.00 | $95.70K | 255,020 | Direct |
| 04 Sep, 2026 | Bryan M Lee | Chief Financial Officer | Disposed S | 6,500 | $33.05 | $214.82K | 303,451 | Direct |
| 04 Sep, 2026 | Tiffany N. Meriweather | Chief Admin. Legal Officer | Disposed S | 5,600 | $33.02 | $184.91K | 266,172 | Direct |
| 04 Sep, 2026 | Andy Dignan | President | Disposed S | 4,379 | $33.51 | $146.74K | 250,641 | Direct |
| 04 Sep, 2026 | Bryan M Lee | Chief Financial Officer | Disposed S | 7,813 | $33.52 | $261.89K | 295,638 | Direct |
| 04 Sep, 2026 | Tiffany N. Meriweather | Chief Admin. Legal Officer | Disposed S | 7,809 | $33.51 | $261.68K | 258,363 | Direct |
| 04 Sep, 2026 | Bryan M Lee | Chief Financial Officer | Disposed S | 4,995 | $33.45 | $167.08K | 290,643 | Direct |
| 08 Sep, 2026 | Tiffany N. Meriweather | Chief Admin. Legal Officer | Disposed S | 5,114 | $31.55 | $161.35K | 253,249 | Direct |
| 04 Sep, 2026 | Andy Dignan | President | Disposed S | 3,295 | $33.45 | $110.22K | 247,346 | Direct |
| 08 Sep, 2026 | Andy Dignan | President | Disposed S | 2,746 | $31.57 | $86.69K | 244,600 | Direct |
| 08 Sep, 2026 | Bryan M Lee | Chief Financial Officer | Disposed S | 1,310 | $32.60 | $42.71K | 289,333 | Direct |
| 03 Sep, 2026 | Leena Mansharamani | Svp, Chief Accounting Officer | Disposed S | 2,558 | $34.19 | $87.46K | 56,476 | Direct |
| 03 Sep, 2026 | Leena Mansharamani | Svp, Chief Accounting Officer | Disposed S | 100 | $35.05 | $3.50K | 56,376 | Direct |
| 04 Sep, 2026 | Leena Mansharamani | Svp, Chief Accounting Officer | Disposed S | 2,505 | $33.32 | $83.47K | 53,871 | Direct |
| 04 Sep, 2026 | Leena Mansharamani | Svp, Chief Accounting Officer | Disposed S | 201 | $33.71 | $6.78K | 53,670 | Direct |
| 08 Sep, 2026 | Leena Mansharamani | Svp, Chief Accounting Officer | Disposed S | 1,253 | $31.53 | $39.51K | 52,417 | Direct |
| 28 Aug, 2026 | Andy Dignan | President | Disposed S | 17,767 | $35.03 | $622.38K | 257,920 | Direct |
| 13 Jul, 2026 | Niranjan Vijayaragavan | Chief Technology Officer | Acquired A | 207,734 | $0.00 | $0 | 207,734 | Direct |
| 13 Jul, 2026 | Robert Hornish | Chief Sales Officer | Acquired A | 121,444 | $0.00 | $0 | 121,444 | Direct |