<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0202</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2005-02-01</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0001299688</issuerCik>
        <issuerName>optionsXpress Holdings, Inc.</issuerName>
        <issuerTradingSymbol>OXPS</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0000830588</rptOwnerCik>
            <rptOwnerName>SUMMIT PARTNERS L P</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>222 BERKELEY STREET</rptOwnerStreet1>
            <rptOwnerStreet2>18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>Mang Mbr of GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001258825</rptOwnerCik>
            <rptOwnerName>SUMMIT PARTNERS VI GP LLC</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>222 BERKELEY STREET</rptOwnerStreet1>
            <rptOwnerStreet2>18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>Indirect GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001258826</rptOwnerCik>
            <rptOwnerName>SUMMIT PARTNERS VI GP LP</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>222 BERKELEY STREET</rptOwnerStreet1>
            <rptOwnerStreet2>18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001255670</rptOwnerCik>
            <rptOwnerName>COLLINS SCOTT C</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O SUMMIT PARTNERS</rptOwnerStreet1>
            <rptOwnerStreet2>222 BERKELEY STREET, 18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>Indirect GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001255672</rptOwnerCik>
            <rptOwnerName>MOHAN KEVIN P</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O SUMMIT PARTNERS</rptOwnerStreet1>
            <rptOwnerStreet2>222 BERKELEY STREET, 18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>Indirect GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001256100</rptOwnerCik>
            <rptOwnerName>WALSH ROBERT V</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>C/O SUMMIT PARTNERS</rptOwnerStreet1>
            <rptOwnerStreet2>222 BERKELEY STREET, 18TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>BOSTON</rptOwnerCity>
            <rptOwnerState>MA</rptOwnerState>
            <rptOwnerZipCode>02116</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>1</isOther>
            <officerTitle></officerTitle>
            <otherText>Indirect GP of 10% Owner</otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2005-02-01</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>C</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>18196074</value>
                    <footnoteId id="F1"/>
                </transactionShares>
                <transactionPricePerShare>
                    <footnoteId id="F2"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>18328489</value>
                    <footnoteId id="F3"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Mang Mbr of GP of 10% Owner</value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2005-02-01</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>4500000</value>
                    <footnoteId id="F4"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>15.345</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>13828489</value>
                    <footnoteId id="F5"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Mang Mbr of GP of 10% Owner</value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Series A Preferred Stock</value>
            </securityTitle>
            <conversionOrExercisePrice>
                <footnoteId id="F2"/>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2005-02-01</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>C</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>18196074</value>
                    <footnoteId id="F1"/>
                </transactionShares>
                <transactionPricePerShare>
                    <footnoteId id="F2"/>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <footnoteId id="F2"/>
            </exerciseDate>
            <expirationDate>
                <footnoteId id="F2"/>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>18196074</value>
                    <footnoteId id="F1"/>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>0</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>Mang Mbr of GP of 10% Owner</value>
                </natureOfOwnership>
            </ownershipNature>
        </derivativeTransaction>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">Shares are held as follows:  12,333,000 shares in the name of Summit Ventures VI-A, L.P.; 5,143,358 shares in the name of Summit Ventures VI-B, L.P.; 256,493 shares in the name of Summit VI Advisors Fund, L.P.; 393,803 shares in the name of Summit VI Entrepreneurs Fund, L.P.; and 69,420 shares in the name of Summit Investors VI, L.P.</footnote>
        <footnote id="F2">Each share of Series A Preferred Stock was converted into one(1) share of Common Stock upon the completion of OXPS' initial public offering.  There was no expiration date.</footnote>
        <footnote id="F3">Shares are held as follows:  12,422,748 shares in the name of Summit Ventures VI-A, L.P.; 5,180,790 shares in the name of Summit Ventures VI-B, L.P.; 258,360 shares in the name of Summit VI Advisors Fund, L.P.; 396,668 shares in the name of Summit VI Entrepreneurs Fund, L.P.; and 69,923 shares in the name of Summit Investors VI, L.P.</footnote>
        <footnote id="F4">Shares are held as follows:  3,050,026 shares in the name of Summit Ventures VI-A, L.P.; 1,271,984 shares in the name of Summit Ventures VI-B, L.P.; 63,432 shares in the name of Summit VI Advisors Fund, L.P.; 97,390 shares in the name of Summit VI Entrepreneurs Fund, L.P.; and 17,168 shares in the name of Summit Investors VI, L.P.</footnote>
        <footnote id="F5">Shares are held as follows:  9,372,722 shares in the name of Summit Ventures VI-A, L.P.; 3,908,806 shares in the name of Summit Ventures VI-B, L.P.; 194,928 shares in the name of Summit VI Advisors Fund, L.P.; 299,278 shares in the name of Summit VI Entrepreneurs Fund, L.P.; and 52,755 shares in the name of Summit Investors VI, L.P.</footnote>
    </footnotes>

    <remarks>The entities mentioned in Footnotes 1, 3, 4 and 5 are collectively referred to as &quot;Summit Partners&quot;.  Summit Partners, L.P. is the managing member of Summit Partners VI (GP), LLC, which is the general partner of Summit Partners VI (GP), L.P., which is the general partner of each of Summit Ventures VI-A, L.P., Summit Ventures VI-B, L.P., Summit VI Advisors Fund, L.P., Summit VI Entrepreneurs Fund, L.P. and Summit Investors VI, L.P.  Messrs. Collins, Mohan and Walsh, along with Peter Y. Chung, Bruce R. Evans, Walter G. Kortschak, Martin J. Mannion, Thomas S. Roberts, E. Roe Stamps, IV, Joseph F. Trustey, Stephen G. Woodsum and Gregory M. Avis (who are included in a separate report due to the restriction on the number of joint filers in an electronic report), are the members of Summit Master Company, LLC, which is the general partner of Summit Partners, L.P., and each disclaims beneficial ownership of the shares held by Summit Partners, except to the extent of his pecuniary interest therein.</remarks>

    <ownerSignature>
        <signatureName>Summit Partners, L.P., by Summit Master Company, LLC, Its General Partner, by Robin W. Devereux, Power of Attorney for Martin J. Mannion, Member</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>Summit Partners VI (GP), LLC, by Robin W. Devereux, Power of Attorney for Martin J. Mannion, Member</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>Summit Partners VI (GP), L.P., by Summit Partners VI (GP), LLC, Its General Partner, by Robin W. Devereux, Power of Attorney for Martin J. Mannion, Member</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>Robin W. Devereux, Power of Attorney for Scott C. Collins</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>Robin W. Devereux, Power of Attorney for Kevin P. Mohan</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>

    <ownerSignature>
        <signatureName>Robin W. Devereux, Power of Attorney for Robert V. Walsh</signatureName>
        <signatureDate>2005-02-03</signatureDate>
    </ownerSignature>
</ownershipDocument>

