Nicholas S.

SLED SaaS Enterprise Account Executive | GovTech 1x Exit | Short-Term Rental SME

Toronto, Ontario, Canada

About

Why read about me? TL;DR I bring in the 7-figure SaaS ARR, I have the technical know-how to dive deeper with SLED clients, and I build the playbook when one doesn’t exist. Long Version: Growing up in Silicon Valley, I developed a natural curiosity for software and business. Today, I am an Enterprise Account Executive with a strong Solutions Engineering and Product Management background focused on bridging the gap between complex SaaS solutions and the leaders who need them. Currently, I help organizations build their GTM strategy and leverage AI to solve their hardest growth challenges. Previously, I spent almost a decade in the STR permit/tax compliance and fraud space. I have led cross functional teams of over 100 across sales, customer success, product, data, and operations. Some key highlights include: • Closing: Closed over 20 enterprise property tax and compliance SaaS deals ($500K–$1.5M+ annual) and over 100 SMB B2G deals • Upselling: Expanded a $50K pilot into an $800K full-suite enterprise program achieving 1500% revenue growth • Retention: Retained $1M/yr at-risk client by building a 300% ROI model, converting annual renewal into a 3-year contract • GTM: Scaled B2G short term rental tax fraud SaaS startup to acquisition as Head of GTM & Product Manager I have exceeded multimillion dollar quotas, won seven figure competitive RFP bids, and helped scale teams and processes that improved revenue performance. I take an intrapreneurial approach. If a playbook does not exist, I build it. If a process slows sales down, I fix it. When I am not at work, I am usually with my spoiled German Spitz, on a plane exploring new places, or eating good! Always looking to connect with new folks, events and opportunities!

Experience

  • Founder at Such-a-Diva Group
    Jun 2014 - Present · 12 yrs 1 mo

    Boutique Sales and GTM Consulting Firm Current Clients Include: EdTech AI, STR AI, Govtech AI, Logistics AI, Retail AI

  • Account Executive and Enterprise Solutions Engineer at Avenu Insights & Analytics
    Nov 2022 - Jun 2025 · 2 yrs 8 mos

    • Closed over 20 enterprise public-sector SaaS deals ($500K–$1.5M+ annual) and over 100 SMB B2G deals across Avenu and Harmari • Expanded a $50K pilot into an $800K full-suite enterprise program achieving 1500% revenue growth • Solely retained $1M/yr at-risk client by building a 300% ROI model, converting annual renewal into a 3-year contract • Exceeded 2023 quota at 110%, managing a $50M+ enterprise public sector pipeline in Salesforce for forecasting. • Sold a $1.65M 3-year deal by leading architecture deep dives for city departments and public stakeholders, overcoming technical and procedural objections. • Conducted 10+ SaaS product demos per week, achieving a 98% conversion to proposal; managed 40+ RFPs and unsolicited bids monthly with a 90% shortlist success rate. • Evaluated 100+ prospect API architectures (REST) and successfully recommended ETL solutions during buildouts. • Designed and positioned AI and automation strategies that replaced manual analyst processes with intelligent matching algorithms, reducing workload by ~50% and delivering significant cost savings. • Managed and coached a BDR producing 200+ outbound calls per week, improving meeting conversion by 50% and influencing $20M+ in pipeline. • Authored and negotiated technical SOWs and compliance responses, ensuring alignment with SOC 2, SSO, and data privacy standards. • Built Power BI dashboards for government transparency and reporting requirements; drove design of a public-facing portal Skills & Expertise: Public Sector Sales, Enterprise SaaS, SLED Sales, Compliance Software, Tax Fraud Detection, Technical Selling, Solution Architecture, RFP & Proposal Writing, SaaS Product Demonstration, API Integration (REST), Salesforce, Assembla, Outreach, AI & Automation Strategy, Pipeline Management, Technical SOWs, SOC 2 & Data Privacy Compliance, BDR Coaching, Revenue Growth

  • Harmari by LTAS Technologies (4 yrs 6 mos)
    • Head of GTM
      Aug 2021 - Nov 2022 · 1 yr 4 mos

      Short Term Rental Tax and Permit Compliance Software Acquisition: • Acted as right-hand to the CEO supporting a successful acquisition of the company. Sales & Business Development: • Closed 30 new government clients and supported the acquisition of numerous additional accounts, securing five- and six-figure deals and expanding recurring revenue. • Managed 3 person BDR and sales operations team creating lead-gen and revenue operations systems that generated 5 discovery calls a week • Conducted lead generation, demos, quotes, proposals, and RFPs, including rewriting company templates. • Educated hundreds of public servants through presentations at 25+ conferences. Product Management: • Headed STR product team, managing multiple analysts. • Researched, proposed, pre-sold, and developed a new PaaS product from the ground up. • Redesigned entire STR PaaS product based on 50+ in-person user interviews, from feedback to prototype. • Proposed and developed multiple new software features and internal tools. • Restructured pricing model, including new premium modules for tiered offerings. Customer Success: • Managed 100+ clients and 3 associates; onboarded and trained 30+ new clients. • Upsold clients during training and shifted customer success operations from email to ticketing system. • Reduced first response times by 48% and average ticket handling time by 53%. • Redesigned onboarding process and help guide. Skills & Expertise: Product Management, Skiptracing, Customer Success Management, Client Onboarding, Upselling, Tax Fraud Research, Lead Generation, Cold Outreach, RFP Management Technical Tools & Systems: Zendesk, Pipedrive, Mailchimp, Canva, Adobe, SQL

    • Sabattical
      Apr 2020 - Aug 2021 · 1 yr 5 mos

      Completed a planned sabbatical to finalize coursework at UofT Rotman while broadening skills through internships and part-time roles

    • Research Analyst Manager
      Sep 2018 - Apr 2020 · 1 yr 8 mos

      I recommended, built, and led cross-functional research, analytics, and marketing initiatives. Research & Operations: • Recommended and built a 60-person research team focused on investigating STR compliance and tax fraud. • Managed 2 business analysts focused on pricing strategy and loss tax revenue analysis, identifying $2.6M in uncollected tax revenue. • Reduced labor costs by 50% while scaling investigative capacity and maintaining output. • Designed and implemented team structure, hiring, and training programs to scale investigative capabilities efficiently. • Oversaw day-to-day operations of the analyst team, ensuring high-quality research and accurate compliance reporting. • Developed standardized processes and workflows to increase efficiency and consistency across investigations. • Implemented performance metrics and reporting dashboards to monitor productivity and outcomes. • Mentored and coached analysts, fostering skill development and knowledge sharing across the team. Marketing: • Managed 2 marketing associates, overseeing all marketing initiatives for 4 products. • Created websites, logos, white papers, case studies, and print marketing materials. • Increased monthly newsletter open rates by 11.5% and click-through rates by 7.2%.

  • Product Manager at BlackBerry
    Sep 2021 - Jan 2022 · 5 mos

    • Led a team of 3 interns in executing product initiatives and supporting project deliverables for federal SaaS product. • Designed and implemented a beta test community to gather user data and determine market fit for a B2G product. • Developed competitive analysis reports and managed product fulfillment using Salesforce, JIRA, and Confluence; conducted QA testing. • Ran weekly 30-person multi-department meetings to provide client and project support. Skills & Tools: Product Management, B2G Strategy, Beta Testing, QA Testing, Competitive Analysis, Team Leadership, Salesforce, JIRA, Confluence

  • Lead Information Security Analyst at University of Toronto
    May 2021 - Aug 2021 · 4 mos

    • Managed a team of 3 analysts, overseeing 100+ helpdesk tickets per week and improving SLA compliance and ServiceNow response metrics. • Built strategic reporting dashboards in Tableau and ServiceNow for the CISO office, enabling better security operations planning and executive decision-making. • Led Identity and Access Management (IAM) initiatives and provided cross-departmental helpdesk support across 6 IS channels. • Extracted, analyzed, and summarized data for monthly performance reports presented to management including the CISO, Director, and Managers. Skills & Tools: Team Leadership, Identity & Access Management (IAM), HelpDesk Operations, SLA Compliance, Data Analysis, Reporting, Tableau, ServiceNow, Security Operations