Account Executive - Enterprise at AISquared

<p data-start="218" data-end="239"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="218" data-end="239">Position Overview</strong></span></p> <p data-start="241" data-end="1039"><span style="font-family: tahoma, arial, helvetica, sans-serif;">We are seeking a dynamic and results-driven Strategic Account Executive to focus on acquiring new customers and expanding our market presence in the enterprise segment. In this role, you will help large, complex organizations adopt and scale our cutting-edge data, AI, and analytics platform to drive transformation at scale. You will own the entire sales cycle, from strategic prospecting to contract execution and work closely with senior technical and business stakeholders to deliver high-impact, tailored solutions. This role is pivotal in driving revenue growth through the pursuit, development, and closure of high-value enterprise opportunities. The ideal candidate thrives in highly complex sales environments, is trusted at the executive level, and knows how to move big deals forward.</span></p> <p data-start="1046" data-end="1070"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1046" data-end="1070">Key Responsibilities</strong></span></p> <ul data-start="1072" data-end="2608"> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1072" data-end="1230"> <p data-start="1074" data-end="1230"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1074" data-end="1114">Enterprise New Business Development:</strong><span class="Apple-converted-space">&nbsp;</span>Identify, qualify, and pursue large-scale enterprise opportunities to secure new logos and major expansion deals.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1231" data-end="1392"> <p data-start="1233" data-end="1392"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1233" data-end="1254">Solution Selling:</strong><span class="Apple-converted-space">&nbsp;</span>Use a consultative, value-based approach to diagnose enterprise challenges and align our platform to business and technical objectives.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1393" data-end="1534"> <p data-start="1395" data-end="1534"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1395" data-end="1420">Executive Engagement:</strong><span class="Apple-converted-space">&nbsp;</span>Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1535" data-end="1687"> <p data-start="1537" data-end="1687"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1537" data-end="1571">Strategic Pipeline Management:</strong><span class="Apple-converted-space">&nbsp;</span>Develop and manage a strong, high-value pipeline with clear deal strategy, close plans, and accurate forecasting.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1688" data-end="1833"> <p data-start="1690" data-end="1833"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1690" data-end="1715">Targeted Prospecting:</strong><span class="Apple-converted-space">&nbsp;</span>Execute strategic outreach including account-based selling, executive-level networking, and event-based engagement.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="1834" data-end="2029"> <p data-start="1836" data-end="2029"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="1836" data-end="1871">Complex Sales Cycle Management:</strong><span class="Apple-converted-space">&nbsp;</span>Lead all phases of multi-stakeholder, multi-month enterprise sales cycles including discovery, demos, proposals, business cases, negotiations, and closure.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="2030" data-end="2184"> <p data-start="2032" data-end="2184"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2032" data-end="2066">Market &amp; Account Intelligence:</strong><span class="Apple-converted-space">&nbsp;</span>Monitor industry trends, account priorities, budgets, and competitive activity to identify and shape opportunities.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="2185" data-end="2346"> <p data-start="2187" data-end="2346"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2187" data-end="2219">Cross-Functional Leadership:</strong><span class="Apple-converted-space">&nbsp;</span>Partner with marketing, product, customer success, and leadership to support enterprise deal strategy and post-sale success.</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="2347" data-end="2496"> <p data-start="2349" data-end="2496"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2349" data-end="2368">CRM Discipline:</strong><span class="Apple-converted-space">&nbsp;</span>Maintain detailed and accurate activity, pipeline, and account information in CRM systems (Salesforce/HubSpot or equivalent).</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="2497" data-end="2608"> <p data-start="2499" data-end="2608"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2499" data-end="2523">Revenue Performance:</strong><span class="Apple-converted-space">&nbsp;</span>Consistently meet or exceed enterprise quota targets and key performance indicators.</span></p> </li> </ul> <p data-start="2615" data-end="2633"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2615" data-end="2633">Qualifications</strong></span></p> <p data-start="2635" data-end="2716"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2635" data-end="2648">Location:</strong><span class="Apple-converted-space">&nbsp; Remote with a high preference for candidates within the NYC &amp; Chicago metro area(s).&nbsp;</span></span></p> <p data-start="2718" data-end="2907"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2718" data-end="2732">Experience</strong></span><br data-start="2732" data-end="2735"><span style="font-family: tahoma, arial, helvetica, sans-serif;">10+ years of enterprise sales experience with a strong record of closing large, complex deals (6–7+ figure ACVs), preferably selling SaaS, data, AI, or analytics platforms.</span></p> <p data-start="2909" data-end="3001"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="2909" data-end="2922">Education</strong></span><br data-start="2922" data-end="2925"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Bachelor’s degree in business, marketing, or a related field; MBA is a plus.</span></p> <p data-start="3008" data-end="3018"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="3008" data-end="3018">Skills</strong></span></p> <ul data-start="3020" data-end="3889"> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3020" data-end="3101"> <p data-start="3022" data-end="3101"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Proven ability to prospect, develop, and close enterprise level opportunities</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3102" data-end="3180"> <p data-start="3104" data-end="3180"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Experience managing full cycle, multi stakeholder enterprise sales motions</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3181" data-end="3267"> <p data-start="3183" data-end="3267"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Strong command of structured sales methodologies (MEDDICC, Challenger, Spin, etc.)</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3268" data-end="3337"> <p data-start="3270" data-end="3337"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Executive level communication, presentation, and influence skills</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3338" data-end="3418"> <p data-start="3340" data-end="3418"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Proven ability to navigate complex buying groups and long procurement cycles</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3419" data-end="3489"> <p data-start="3421" data-end="3489"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Expertise in building business cases and articulating ROI at scale</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3490" data-end="3560"> <p data-start="3492" data-end="3560"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Comfortable delivering executive-level demos and strategy sessions</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3561" data-end="3646"> <p data-start="3563" data-end="3646"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Strong negotiation and closing abilities, including contract and pricing strategy</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3647" data-end="3730"> <p data-start="3649" data-end="3730"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Deep familiarity with SaaS models, multi-year contracts, and expansion planning</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3731" data-end="3798"> <p data-start="3733" data-end="3798"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Advanced CRM, pipeline management, and forecasting capabilities</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3799" data-end="3889"> <p data-start="3801" data-end="3889"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Ability to manage a small number of high-impact accounts with precision and discipline</span></p> </li> </ul> <p data-start="3896" data-end="3910"><span style="font-family: tahoma, arial, helvetica, sans-serif;"><strong data-start="3896" data-end="3910">Attributes</strong></span></p> <ul data-start="3912" data-end="4620"> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3912" data-end="3973"> <p data-start="3914" data-end="3973"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Confident, strategic, and credible with senior executives</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="3974" data-end="4039"> <p data-start="3976" data-end="4039"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Results-obsessed with a strong sense of urgency and ownership</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4040" data-end="4121"> <p data-start="4042" data-end="4121"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Highly resilient and comfortable operating in ambiguity and long sales cycles</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4122" data-end="4191"> <p data-start="4124" data-end="4191"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Strategic thinker with the ability to execute at a tactical level</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4192" data-end="4266"> <p data-start="4194" data-end="4266"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Organized, disciplined, and detail-oriented with strong follow-through</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4267" data-end="4326"> <p data-start="4269" data-end="4326"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Curious, commercially sharp, and continuously improving</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4327" data-end="4403"> <p data-start="4329" data-end="4403"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Comfortable being the quarterback for large, cross-functional deal teams</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4404" data-end="4474"> <p data-start="4406" data-end="4474"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Polished, professional, and trusted both internally and externally</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4475" data-end="4549"> <p data-start="4477" data-end="4549"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Collaborative but fully capable of running complex deals independently</span></p> </li> <li style="font-family: tahoma, arial, helvetica, sans-serif;" data-start="4550" data-end="4620"> <p data-start="4552" data-end="4620"><span style="font-family: tahoma, arial, helvetica, sans-serif;">Composed under pressure and able to keep momentum through setbacks</span></p> </li> </ul>