Stewart Mackay

Senior Account Executive, CPaaS and Voice AI

I sell messaging, voice and authentication platforms to enterprises. Above quota every year from 2017 to 2025.

London, United Kingdom

Portrait of Stewart Mackay

Track record

Annual quota attainment, 2017 to 2025 Dashed line: 100% of quota 117% 2017 132% 2018 105% 2019 122% 2020 105% 2021 109% 2022 203% 2023 168% 2024 172% 2025 President's Club CM.com SentiOne+ Twilio Twilio
View as a table
YearEmployerAttainment
2017CM.com117%
2018CM.com132%
2019CM.com105%
2020CM.com122%
2021CM.com105%
2022CM.com109%
2023SentiOne and Twilio, combined203%
2024Twilio168%
2025Twilio172%

Basis: annual ACV quota of $1M to $2M. 2023 combines SentiOne and Twilio.

Experience

  1. Dec 2023 to Nov 2026

    Twilio

    Senior Account Executive from March 2026, previously Account Executive, New Business

    President's Club 2025. Led enterprise deals across messaging, voice, email and customer data.

  2. May to Nov 2023

    SentiOne

    Regional Sales Lead

    Signed the company's first UK Voice AI deal. Built the full pricing proposition, turning token usage into per-minute and per-conversation rates and thresholds.

  3. Oct 2016 to May 2023

    CM.com

    Business Development Manager, then Senior BDM and Team Lead, New Business and Account Management

    Above quota every year from 2017 to 2022. Signed the largest global enterprise user of CM.com's voice product. Mentored AEs and SDRs.

  4. Nov 2002 to Oct 2006

    VeriSign

    Inside Sales Executive, then Territory Sales Manager, Enterprise

    110%+ every quarter as Territory Sales Manager, 188% in the final quarter. President's Club three years running.

  5. 2006 to 2016

    Channel and enterprise sales, South Africa

    KnowledgeTree, Cash Crusaders, Nashua, Anderson Group, MICROmega, Magic Software, Mblox, Network Sunday

    Channel sales manager roles including East and West Africa. Earlier, general manager of 11 retail stores.

Leadership in practice

I want to move into sales leadership, and I have already done part of the job. At CM.com I led a new-business team, mentored AEs and SDRs, and built the processes and partner channels others sold through.

Team Lead, New Business and Account Management, CM.com, 2021 to 2022.

Carried my own quota while leading the team's revenue and gross-profit quota.

Above 100% on both individual and team quotas.

AEs, SDRs and account managers on my team at CM.com.

Mentored, trained and managed them, and defined the lead generation, qualification and CRM process.

Team performance above 100% for both new business and Account Manager revenue attainment. A colleague called me "a great leader and mentor" (Simon Fear, 2023).

Senior Business Development Manager, CM.com, 2019 to 2021.

Built a channel partner ecosystem and signed new carrier relationships in Kenya and Nigeria.

More new logos signed through channel, and lower carrier costs with better profitability.

APIs & IPAs London, a developer community meetup I have designed and plan to launch in the coming months - it will be a regular pub meetup in London for Developers & Product Managers.

Not yet launched.

Triathlon and endurance running coach at Embark (South Africa), 2013 to 2017, alongside my sales roles.

Coached hundreds of beginner and intermediate athletes to Ironman 70.3 and full Ironman finishes. I have also finished Ironman South Africa and Ironman Mallorca, with a 70.3 best of 5:14 at Durban.

Every athlete I coached reached their goal of finishing, including total beginners who could not swim or had never ridden a bicycle.

Domain depth

CPaaS stack

SMS, WhatsApp, Programmable Voice (SIP and IVR), SendGrid email, Verify, Segment CDP and Twilio Flex. Number provisioning, TrustHub and deliverability.

Voice AI

Voice AI, ConversationRelay and Conversation Intelligence. I built my own AI-assisted sales tooling, including voice AI benchmarking.

Authentication and compliance

OTP, 2FA and MFA, KYC and AML, WhatsApp Business, and telecom and data regulation.

Selected wins

My largest deals in the last 12 months. Customers are anonymised.

Major UK telecommunications provider, messaging

$1.5M ACV

UK systems integrator, Voice AI

Multi-year deal

UK marketplace leader

$500k ACV

Listed UK financial services enterprise, multi-factor authentication

$400k ACV

Customers

This is a snapshot, not an exhaustive list. I have sold to hundreds of customers across these verticals in South Africa, the UK, Ireland, the UAE and the United States.

  • State Street
  • CitiStreet
  • London Stock Exchange
  • Equiniti
  • Funding Circle
  • Zilch Technology Group
  • Yoti
  • Radius Payment Solutions
  • OUTSurance
  • Discovery Holdings
  • HelloPaisa
  • Etisalat
  • Gamma Communications
  • Link Mobility
  • SMSPortal
  • KFC / Yum! Brands
  • Colgate-Palmolive
  • Sears
  • Hollywood Bowl Group
  • Checkatrade
  • Flutter Entertainment
  • Boylesports
  • SportPesa
  • Google
  • WPP
  • YouGov
  • RLDatix
  • incident.io
  • Bromcom
  • Talkative
  • Nutun
  • Haysto
  • NASA
  • University of California
  • Caltech
  • Purdue University
  • MIT

Customer stories

KFC South Africa (Yum! Brands)

A WhatsApp ordering channel with click-and-collect, built on CM.com's WhatsApp Business API. The story describes it as a first for South African fast food, with usage growing month on month. I am quoted in it as Team Lead, New Business and Account Management.

Read the CM.com story

Hello Paisa

A WhatsApp chatbot that handles KYC and money transfers, plus SMS, number verification and a shared agent inbox. Customers send money over WhatsApp data instead of SMS bundles, which the story says makes it cheaper.

Read the CM.com story

CompareGuru

A shared inbox joining WhatsApp and Facebook Messenger into one place for an insurance comparison platform.

CompareGuru's CEO credits it with 20% less human error and 30% better contactability.

Read the CM.com story

References

Stewart is a great sales person who knows how to listen to the client and help them identify their challenges … not only a great sales person, but also a great leader and mentor.
Simon Fear, Communications Architect at Rentokil Initial. Worked on the same team, November 2023.
Stewart is an expert in his field, assisting in setting new standards in customer experience … His expertise … has helped my projects immensely.
Elizma de Beer, Growth Leader in fintech. Client, March 2023.
He has the ability to converse at both Technical and Commercial level.
Sven Theophil, Global Partnerships and Growth Leader. Client, May 2012.

Education, languages and other

  • Computer science at the University of London, in progress, with a focus on AI and machine learning
  • Private Pilot's Licence
  • RYA Competent Crew, and Essential Navigation and Seamanship
  • English (native), Afrikaans (professional working)

Contact

Send a message and I will reply by email. Your details go only to me.