AI Marketing Masters by Annika Helendi

Helping marketers and solopreneurs leverage AI so they could easily do a 5-person job alone. 

Follow my Youtube channel for free automation tutorials and join the AI Marketing Masters community to get access to all the shortcuts - blueprints, templates and prompts.

Founder

astronaut.marketing

Custom SEO-driven growth strategies for B2B SaaS startups in the $1-10M ARR range.
// Strategy creation, consulting and advisory
// Open to fractional CMO roles

Fractional CMO, Growth Consultant, SEO Strategist

Blessed Pirate

Get weekly LinkedIn posts for publishing. Build your personal brand as an expert - https://blessedpirate.com

ContentFly

* Developed and implemented the go-to-market strategy
* Bootstrapped ContentFly to $500k ARR in 2019
* Developed and launched 2 add-on products

Co-Founder & CMO

Dashbird

* Developed and implemented the go-to-market strategy
* Built the initial marketing team
* Raised a seed round of $800k in 2018

Teamweek 

* Took over and lead a 12-person internationally distributed team 
* Revamped the business and turned it profitable in 2 months. 
* Grew the revenue by 100% in 2017 (to $700k ARR).

Toggl

* Generated 1.8 million signups over 4 years without a marketing budget (60% year-over-year growth)
* Put together and lead the initial marketing team
* Worked with cross-functional teams to create growth loops, improve the product experience and customer lifetime value.

Head Of Marketing

🪭AI fangirl. Founder. Marketer.

📌 Helping B2B startups grow since 2012

📌 Generated close to 2 million SEO signups in Toggl (and helped to generate many more millions through my consulting work)

📌Favorite roles: founder, CEO, CMO, fractional CMO, SEO strategist, growth consultant

📌Career highlights: made Teamweek profitable and scaled it to €700k ARR with a fully distributed remote team, raised a seed round for Dashbird, launched a bunch of bootstrapped startups during Covid that all failed, been able to avoid having a boss for over 5 years, worked with over a 100 founders, launched a profitable side-business (Blessed Pirate).

Annika Helendi

Askly

A perfect blend of humans & AI for customer service and sales. Not another annoying chatbot. 

Many customers shifted from Zendesk, Freshdesk, Tidio, Olark, Tawk.to etc to Askly. 

Results: +300% growth in chat usage, less calls and emails. <75% more efficient team. 
The highest customer satisfaction rate in the industry 🏆

If you want to learn more, book a quick demo:
www.askly.me

What people said about Askly demo calls:
"Best spent 30 min"
"The best demo call I've ever had"
"A call full of valuable insights."

Askly can be added to any website in 2 min setup.
Zero development.

See you! 📆

CEO & Founder

Eesti E-kaubanduse Liit

Member of the Management Board

e-Governance Academy

As Estonia gained an international reputation as a leader in e-government, eGA was founded for the creation and transfer of knowledge concerning the development of digital society including e-identity, secure data exchange and cybersecurity.

We have enabled faster e-society, eID, e-services, cyber security and e-democracy development in over 90 countries across the world. 
My role was marketing and export of eID solutions.

Digital Identity Expert

SORACOM Inc.

Soracom provides the cloud-connectivity-as-a-service platform that has integrated mobile communications and cloud services. With teams based in Tokyo, Singapore, Copenhagen and San Francisco we deliver IoT/M2M connectivity at low initial costs and empower many IoT innovators across the world. 

In 2017 Soracom was acquired by KDDI Group for nearly 200M USD.

Director, Marketing and Business Development

SK ID Solutions

We serve and set up e-Identity solutions worldwide. 
SK technology is the backbone of e-ESTONIA and e-RESIDENCY.
> Cross-border secure authentication and digital signature solutions for even the most demanding private and public services. 
> Smart-ID mobile app, reached over 10M transactions monthly
> Mobile-ID, state-recognized eID
> Chip-based solutions such as ID-cards, Enterprise-cards
> Qualified certificates
> Digital Signature software

SK is owned by 3 major Scandinavian companies: Swedbank, SEB and Telia.
Trust and convenience is their everyday business.

Manager, Marketing and Sales Department

Tark Partner

Projects to leverage sales productivity and digitalisation as key enablements of improved performance. 

Our solutions helped various companies like Forus, Alexela, Coop, Tele2 to increase their customer base.

CEO and Co-Founder

U.S. Invest AS

Advisor to the teams of US Invest Holding companies in marketing and sales area. 
US Invest is private investment company with investment portfolio size of 350 MUSD making direct investments in Ukraine, Russia and Baltics.
http://www.usinvest.eu

Adviser

Estonian Entrepreneurship University of Applied Sciences

I was leading the process of rebranding and contributed to restructuration of the company, in addition to managing every-day work of marketing and sales teams (in total team of 30). As a result, 2010 EUAS became the biggest and the most prestigious private university in Estonia (Reference TNS Emor, 2010).

Manager, Marketing & Sales Department

JA Estonia

Software management for internal network and MESE (Management & Economics Simulation Exercise); support the social and economic development among young people; searching for new partners in the EU in cooperation with the Ministry of Economic Affairs and Communications of Estonia.

Manager, Communication & IT

I’m deeply passionate about customer experience and chatbots. Many doubt they work. I prove otherwise.
Today’s customers want fast, genuine help. It’s frustrating to see many brands miss the mark on customer service. 

Customer experience is so much more than just answers or technology. 
It’s about values. It shapes how people feel—both who are receiving and providing support.

We built Askly to bring together AI and human-powered communication in a balanced, high-quality way. 

Askly is a great fit for customer-centric businesses with multilingual customer base.
We’ve enabled 2.5+ million helpful responses in 10+ countries. 

Our customers include hundreds small businesses, but also leading brands like Hilton, Apple, Sportland, Goldtime, Given, ON24, ONOFF, Bauhof, Ballzy, Macta Beauty, etc. 

Get in touch with me here or via chat at www.askly.me 📲💬

Sandra Roosna

Big stage. Big smile. 😁 
Marju Sokman andis mulle võimaluse püstitada oma lavarekordi!

Viimasel ajal, igal üritusel keegi on astunud ligi, maininud mõnda minu postitust, mis neid kõnetas ja arutelu justkui jätkub... (kommenteerige siin palun ikka ka!)

Miks ka seda teen?  
Suur osa, lausa ligi 50% Askly tänavusest kasvust on tulnud just Linkedini ja minu personaalse konto abil.
See näitab, kui oluline on usaldus, personaalne "touch" ja selge kommunikatsioon.

Sotsiaalmeedia ei ole minu jaoks scroll-imise koht.
Püüan pigem luua sisu, mis aitab kedagi ja selgitab, millega saame kasulikud olla. Iga päev on mul kalendris selleks eraldatud 30 minutit. 

Eelmisel nädalal konverentsil “Juht pingeväljas” rääkis Marju nii põnevalt tehisarust, sotsiaalmeediast ja tulevikutrendidest. Jagasin ka oma kogemust.

Arutelu jõudis teemadeni, mis tekitavad kõhedust. 

Generatsioon Alpha (2010 ja edasi) kasvab üles maailmas, kus koostöö robotitega on sama loomulik kui meie jaoks oli interneti kasutama õppimine.

Üks põlvkond õppis internetti.
Järgmine õpib koostööd masinatega.
Sotsiaalmeedia on labor, kus katsetada, mis lendab ja mis mitte. 

Suur tänu korraldusmeeskonnale vinge päeva eest!

Let’s make chatbots finally work | Askly is built by one of your customers | For your customer service & sales team | Perfect human + AI blend |

Our relatioship with time is the king.

Building a business, raising small kids, giving attention to every family member, trying to share values through my own example... it's a lot (to enjoy and feel grateful about!)

My list is long, but nothing extraordinary. Probably yours is long too. 

Recently I realized something so important, that I wanted to share:

There is always time. 
We all have same 24h per days. 
Time is never the problem.
Your energy is.

With the right energy, one hour can lift the whole week. 

I started doing one “energy check-in” every day to train awareness (without thinking of the tasks for today).

Fixing energy first!

Maybe it’s 30 minutes of screen-free time. Or one short walk outside. 
Or going to bed earlier tonight.
Or just a healthier lunch! 😉

One small action that charges your energy =  the greater results in whatever you do. 

How often do you think about your inner battery power level?
What helps you charge it?

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Rahast võib ka Linkedin'is rääkida? Minu arvates sama oluline teema nagu tervis, eneseteostus, suhted, hea uni... 

Olen palju aastaid teadlikult vähendanud palgasõltuvust. "Miks" tööd teha ei tohiks olla raha, vaid ikka maailma paremaks tegemine (vähemalt mina mõtlen ikka veel nii naiivselt).

Jagasin varem ka, et mulle endale tuli suureks üllatuseks, aga võlakirjad osutusid 10 aasta jooksul minu kõige kasumlikumaks investeeringuks. 

Huvitav, et ammu ostetud üürikorterite tootlus osutus madalamaks (üür + väärtuse kasv kombineerituna ca 8-9%, miinus oma aeg ja närvirakud). 

Olen ära proovinud palju erinevaid instrumente. 

Usun, et võlakirjade buum on alles ees ja seetõttu jagan veidi oma kogemust, äkki kasulik.

Kes soovib sel teemal rohkem lugeda, 
siis kirjuta kommentaarina: 
"Võlakiri” 
ja saadan materjali koos oma õppetundidega.  

Seal on selgitused ja küsimused, mida endalt küsida, et oma strateegia paika panna. 

Lisan kommentaaridesse ka ühe artikli. Kasulik lugemine, aga sisaldab veidi turundust. 

See ei ole investeerimissoovitus.
Investeerimisel on alati riskid ning iga inimene peab leidma endale sobiva tee.

E-kaubanduses konkurents on juba meeletu (kuhu edasi?). Viimastel aastatel on klientide ootused kasvanud igal sammul:

Tarne võiks toimuda samal päeval.
Vastust tahetakse kohe.
Soodustustest rääkimata.

Näen, et üks põhimõte alati kehtib:
Klient tuleb hoida oma veebilehel.

Kui ta juba sinu lehele kalli turunduse tulemusena jõudis ja toote vastu huvi tunneb, siis ei tasu teda e-mailile suunata. 

Kiire klienditugi tehisaru abil aitab vähendada hüljatud ostukorvide arvu ja pakkuda paremat kliendikogemust.

Äriotsuseid tehes me ei saa lähtuda sellest, et "mulle juturobotid ei meeldi". 

Tuleb vaadata, mis töötab ja mida inimesed tegelikult ootavad.

Mari Arnover seletab seda oma podcastides "Mida kliendid tahavad" väga hästi. Sain ka jagada oma kogemust. 

Kui teema huvitab, podcasti link on kommentaarina. 😉

Ära ole teenusepakkuja. Ole partner. 
See on kõrgeim tase kliendikogemuses.

Eesti Loto tootejuht Reelika Ein sõnastas selle just nii. 

Askly tarkvara on kujundanud kogenud tootejuhid, paljud klienditoe ja e-kaubanduse tegijad. Nad kõik on mulle suured eeskujud. 👀

Viimastel päevadel saatnud klientidele Askly häälagendi esimese salvestuse (live demo!)

Meil on küll väike tiim, aga need, kellega koos ainuüksi see kuu pead kokku panime... on ikka oma valdkonna tipud!

Võib-olla nii me päriselt muudamegi klienditoe innovaatilisemaks, kiiremaks ja kliendisõbralikumaks. 

Suured tervitused: 
Rode Luhaäär ja Procommerce tiim
Gunnar Obolenski ja Klick tiim
Reelika Ein ja Eesti Loto tiim
Rene Paats ja TKM Finants tiim
Mihkel Sepp ja Rahva Raamat tiim
Sandre Elland ja Confido tiim

graphical user interface, text, application

Uuel nädalal esinen konverentsil "Juht Pingeväljas" Viljandi Kultuuriakadeemias.

Lubati, et ausus, otsekohesus ja mängulisus on konverentsi märksõnad. Lubati ka mikrofon anda. 🎤😊

Räägime sellest, kuidas juhtida, tegutseda ja luua keskkonnas, mis on pidevas vastuolus? Meeletus tehnoloogilises arengutempos. Kus väärtused muutuvad. 

Põnevad arutelud ees. Programmi autorid ja esinejaid nii säravad tegijad: 
Ott Karulin Jorma Sarv, Ivar Põll
Sandra Särav, Taimar Peterkop, Helen Sildna, 
Aivo Adamson, Keiu Virro, Enel Teinemaa, Priit Kallas ✨
Meie paneeli modereerib Viljandi linnapea Johan-Kristjan Konovalov ✨

Kohtumiseni Viljandis 🫶

Somehow full moon makes tech act strange too. To Cloudflare community (all of us here):
mark your calendars with the next full moon date. Take it easy that day. 😉

#cloudflare

When forward-thinking malls raise the customer service bar. 💫 
Ülemiste Center and T1 Tallinn joined Askly and set inspiring example with AI Assistants supporting their teams and customers.

𝐏𝐫𝐨𝐛𝐥𝐞𝐦𝐬 𝐰𝐞 𝐬𝐨𝐥𝐯𝐞 𝐚𝐫𝐞 𝐰𝐞𝐥𝐥 𝐤𝐧𝐨𝐰𝐧:
Modern visitors do not read the website. 
They expect fast replies, across channels.
Multilingual and instant support demands serious resources (even in 3 languages).

We also see every day that the decision to adopt AI in customer service brings real tension. Even inside organisations that usually move fast.

However...
𝐈𝐧 𝐩𝐫𝐚𝐜𝐭𝐢𝐜𝐞 𝐀𝐈 𝐡𝐞𝐥𝐩𝐬 𝐝𝐞𝐥𝐢𝐯𝐞𝐫 𝐟𝐚𝐬𝐭𝐞𝐫 𝐬𝐮𝐩𝐩𝐨𝐫𝐭 + 𝐫𝐞𝐦𝐨𝐯𝐞𝐬 𝐫𝐞𝐩𝐞𝐭𝐢𝐭𝐢𝐯𝐞 𝐰𝐨𝐫𝐤 𝐟𝐫𝐨𝐦 𝐭𝐞𝐚𝐦𝐬.

For full transparency, ofcourse AI gives wrong answers as well.

𝐖𝐞 𝐥𝐨𝐰𝐞𝐫 𝐭𝐡𝐚𝐭 𝐫𝐢𝐬𝐤 𝐰𝐢𝐭𝐡 𝐚 𝐬𝐢𝐦𝐩𝐥𝐞 𝐟𝐥𝐨𝐰:
🔗 A decision engine checks each question against the knowledge base.
⛓️‍💥 If probability to give clear reply drops, AI hands the case to the team.
Every AI reply is clearly marked for full transparency.

𝐀𝐈 𝐚𝐝𝐨𝐩𝐭𝐢𝐨𝐧 𝐢𝐬 𝐚 𝐣𝐨𝐮𝐫𝐧𝐞𝐲.
LLMs impress one moment and confuse the next. But the risk is worth it. 

Below are some examples of Askly in action.
Imagine such answers were typed manually every day. 🤗

Today marked a small milestone: My community is 9000+ people! 🫶 
Feel grateful for everyone following this journey. 

When we have to make any choice "pick the best product, partner, team member..." we want to know who the people are behind the products and brands. 

Therefore, I often share personal beliefs here (when they evolve, and it happens, I share them openly as well). 

This is a short list of who I am today:
▸ Family comes first: relationships with partner, kids and parents is the most important. 
▸ Investing and passive income: for past 10+ years been my path to confidence and peace of mind.
▸ Consistency: For 4+ years I have sent detailed monthly investor updates (I keep hearing I am the only founder in the portfolio doing it). Same with sharing on Linkedin 2+ years.
▸ Moving every day: almost 2 years of 15 minutes of daily exercise (still not easy for me).
▸ When stuck, I go outside and clean the streets: doing something good is my way out.
▸ Charging the battery: one small remote island Hiiumaa is my quiet paradise after tough weeks (there I realize I do not like people as much as it seems).
▸ A bit too self-driven: learning to slow down.
▸ Sometimes hoping for a little appreciation (offer it when you can, it lifts people). 

Professionally: 
Customer experience, innovation and AI are the core interests here.
A world that continues to inspire me every day.

May something here bring a bit more clarity your day and work. And thank you for helping me learn as well!

Just a small Black Friday 2025 survey.
If you bought something today, 
add a 👍 to this post.

If you didn't buy anything, drop a comment (and tell the world how you made it) 😁

Lisaks klienditoe kvaliteedile ja tehisaru kasutamisele on veel üks teema, mille kohta saab öelda, et olen lootusetult “deeply passionate about it” 🥹  See on investeerimine.

Osaliselt tänu Hendrik Roosnale. Tal on suured ideed, mul on korralik filter 😁 

Hiljuti arutasime, et võiksime panna kirja kuidas rahavood tegelikult liiguvad. Just investeerimismaailmas. Lihtsal kujul, et igaüks mõistaks.

Inspiratsiooniks on ühe Haapsalu ilusa uusarenduse pimedad aknad.
Arendaja räägib, et 80 protsenti korteritest on müüdud.
Aga korterites tuled ei põle.

Need pimedad aknad õpetavad rohkem kui enamus investeerimiskursuseid.

Lugu ise on sisuturundus ja Hendrik on Täisteenusliisingu (TTLi) nõukogu liige.
See pole investeerimissoovitus. 
Ise sain selle artikli abil enda pildi palju selgemaks.

taplio

The Battle

Annika Helendi

Sandra Roosna

Followers

Posts

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Performance ScoreSandra Roosna's LinkedIn Performance

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taplio

The Battle

Annika Helendi

Sandra Roosna

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Sandra Roosna's LinkedIn Performance

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Performance ScoreSandra Roosna's LinkedIn Performance