From what you've described, I don't think your problem is that TickTick is a bad task manager. It's that it's fundamentally task-list-first, while your workflow really needs to be calendar-first.

The key requirement you mentioned is this:

"I want something that pushes me to time-box tasks onto my calendar at the start of each day."

That immediately narrows the field. I'd focus on four apps.

1. Sunsama — the best fit for what you described

This is the app I'd recommend first.

Sunsama is almost built around the problem you mentioned.

Instead of dumping you into a huge task list, every morning it walks you through a planning process:

• Review today's tasks
• Pull in tasks from Asana
• Estimate how long they'll take
• Drag them onto your calendar
• Compare planned work against available time
• Commit to a realistic day

It also has an end-of-day shutdown ritual where you intentionally move unfinished work instead of letting it accumulate. That's a big behavioral difference from TickTick. It encourages you to acknowledge that time is limited instead of pretending every task will somehow get done. It integrates with Google Calendar and Asana so you can pull work from existing projects into your daily plan. akiflow.comget-alfred.ai

Downsides

• Expensive
• Manual planning every morning
• Not meant to replace Asana as your project manager

If you enjoy consciously planning your day, that's actually a feature rather than a bug.

2. Akiflow — best if you live in keyboard shortcuts

Akiflow is similar to Sunsama but feels more like a productivity power tool.

It pulls tasks from many sources—including Asana—and treats Google Calendar as the center of your workday.

Its workflow is typically:

• Inbox review
• Choose today's work
• Estimate duration
• Drag tasks into calendar blocks
• Work from today's schedule

Unlike TickTick, the calendar is really the primary interface. Akiflow also includes configurable morning and evening rituals that mirror the workflow you're looking for. akiflow.comproduct.akiflow.comget-alfred.ai

Choose Akiflow if:

• you process lots of Slack messages
• you like keyboard-driven workflows
• you switch between many productivity tools

3. Motion — if you want software to build the schedule

Motion takes a different philosophy.

Instead of asking you to plan your day manually, you tell it:

• priorities
• deadlines
• estimated duration

…and it continuously schedules and reschedules your calendar automatically.

Some people love this.

Others feel like they lose ownership of their day because the software decides when everything happens. Community discussions often frame Motion as an "AI scheduler" rather than a guided daily planner. www.reddit.com

I'd recommend Motion if your biggest pain point is:

"I never know where to fit work between meetings."

rather than

"I want a mindful morning planning ritual."

4. Morgen — if your calendar already runs your life

Morgen is more calendar-centric than task-centric.

It has excellent Google Calendar support and time-blocking without trying to become a full project management system.

It's cleaner than Motion and lighter than Sunsama.

The tradeoff is that it isn't as focused on creating a structured morning planning habit.

Based on your workflow

You said:

• 300-person company
• knowledge work
• Asana already exists
• Google Calendar
• tasks routinely go unfinished because they're never scheduled

That tells me you probably don't need another project manager.

You need a daily execution layer sitting on top of Asana.

That's exactly the niche Sunsama and Akiflow occupy.

My recommendation

🥇 Sunsama if your goal is to build a consistent daily planning ritual. It deliberately slows you down just enough to decide what fits into today, estimate effort, and place work on your calendar before you begin. That sounds closely aligned with the habit you're trying to build. akiflow.comproduct.akiflow.comget-alfred.ai

🥈 Akiflow if you prefer speed, keyboard shortcuts, and aggregating tasks from many sources while still planning your day on a calendar. product.akiflow.com

If I were moving from TickTick in your situation, I'd spend one week trialing Sunsama and one week trialing Akiflow using the exact same Asana projects and Google Calendar. By the end of two weeks, you'll likely know whether you prefer a guided, reflective planning ritual (Sunsama) or a faster, inbox-and-calendar workflow (Akiflow).

If your main problem is “my task list is full, but my calendar is empty”, I would not replace TickTick with another traditional task manager. You’re looking for a daily planner / time-blocking system: something that forces a morning ritual where you choose what matters, estimate time, and put work onto your calendar.

For a 300-person knowledge-work environment with Google Calendar + Asana, these are the strongest alternatives:

ToolBest forWhy it fits your problemWatch-outsSunsamaA guided daily planning ritualProbably the closest match to “plan my day before I start”More expensive; intentionally slower/more reflectiveAkiflowFast task-to-calendar executionExcellent if you want to drag tasks into time blocks quicklyLess of a coaching/planning ritual than SunsamaMotionAutomatic schedulingBest if you want software to decide when tasks happenCan feel less intentional; you give up some controlRoutinePersonal operating system styleCombines habits, tasks, calendar, routinesLess proven for company workflowsTodoist + calendar workflowSimple task managementBetter task database than many plannersRequires more discipline to time-block

1. Best overall fit: Sunsama

Sunsama is the one I would test first for your situation.

Its core workflow is:

• Open daily planning.

• Review unfinished items.

• Pick realistic tasks for today.

• Estimate duration.

• Drag them into calendar slots.

• Execute against the schedule.

That directly addresses your failure mode: a task list lets you postpone indefinitely; a time block creates a commitment. Sunsama explicitly supports guided daily planning, timeboxing tasks to calendars, and pulling work from tools like Asana. Sunsama (+1 more citation)

Why it fits a knowledge worker:

• Great for balancing meetings + deep work.

• Makes “how much can I realistically do today?” part of the workflow.

• Works well when Asana remains the team/project system of record.

• Google Calendar integration lets you plan around meetings rather than pretending you have 8 free hours. Sunsama User Manual (+1 more citation)

Ideal setup:

• Asana = team commitments/projects.

• Sunsama = your personal daily execution layer.

• Google Calendar = the source of truth for time.

2. Best if you want speed: Akiflow

Akiflow is better if your morning ritual is more:

“Show me everything I need to do; I’ll quickly assign time slots.”

It pulls in tasks and lets you organize them alongside your calendar. Its Asana integration imports tasks and supports planning them with deadlines/scheduled dates. Akiflow (+1 more citation)

Choose Akiflow if:

• You dislike slower reflection workflows.

• You process lots of incoming tasks.

• You want keyboard shortcuts and rapid scheduling.

• Your main issue is “I forget to put work on my calendar.”

Choose Sunsama instead if:

• You want a deliberate “start my day” ritual.

• You regularly overcommit.

• You need help deciding what not to do.

3. Best if you want AI scheduling: Motion

Motion takes a different philosophy:

“Tell me what needs doing, and I’ll arrange the day.”

It is attractive if you have many c